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【结 构 式】 
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【分子编号】35535 【品名】3,5-dichloropyridine 【CA登记号】2457-47-8 |
【 分 子 式 】C5H3Cl2N 【 分 子 量 】147.99096 【元素组成】C 40.58% H 2.04% Cl 47.91% N 9.46% |
合成路线1
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate by means of lithium diisopropylamide (LDA) in THF gives 3,5-dichloropyridine-4-carbaldehyde (II), which is condensed with p-thiocresol (III) by means of K2CO3 in DMF (or t-BuOK in THF) yielding 3-chloro-5-(4-methylphenylsulfanyl)pyridine-4-carbaldehyde (IV). The cyclization of (IV) with methylthioglycolate (V) by means of K2CO3 in DMF affords 4-(4-methylphenylsulfanyl)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VI), which is finally treated with ammonia in methanol to obtain the target amide. Alternatively, The hydrolysis of the methyl ester (VI) with LiOH in hot isopropanol/water gives the corresponding free acid (VII), which is treated with oxalyl chloride in dichloromethane to obtain the acyl chloride (VIII). Finally, this compound is treated with NH4OH in THF/water to afford the target amide.
| 【1】 Boyd, S.A.; Stewart, A.O.; Bhatia, P.A.; et al.; Discovery of inhibitors of cell adhesion molecule expression in human endothelial cells: Selective inhibition of ICAM-1 and E-selectin expression. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 73. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (III) | 25437 | 4-methylphenylhydrosulfide | 106-45-6 | C7H8S | 详情 | 详情 |
| (IV) | 35537 | 3-chloro-5-[(4-methylphenyl)sulfanyl]isonicotinaldehyde | C13H10ClNOS | 详情 | 详情 | |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 35538 | methyl 4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridine-2-carboxylate | C16H13NO2S2 | 详情 | 详情 | |
| (VII) | 35539 | 4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridine-2-carboxylic acid | C15H11NO2S2 | 详情 | 详情 | |
| (VIII) | 35540 | 4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridine-2-carbonyl chloride | C15H10ClNOS2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate by means of lithium diisopropylamide (LDA) in THF gives 3,5-dichloropyridine-4-carbaldehyde (II), which is condensed with p-thiocresol (III) by means of K2CO3 in DMF (or t-BuOK in THF) yielding 3-chloro-5-(4-methylphenylsulfanyl)pyridine-4-carbaldehyde (IV). The cyclization of (IV) with methyl thioglycolate (V) by means of K2CO3 in DMF affords 4-(4-methylphenylsulfanyl)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VI), which is finally condensed with 2,3-dihydroxypropylamine (VII) by means of NaH in DMF to obtain the target amide. Alternatively, The hydrolysis of the methyl ester (VI) with LiOH in hot isopropanol/water gives the corresponding free acid (VIII), which is treated with N-hydroxysuccinimide (IX) and DCC in dichloromethane to obtain the activated ester (X). Finally, this compound is treated with 2,3-dihydroxypropylamine (VII) in dioxane/methanol to afford the target amide. The activation of the acid (VIII) can also be performed with oxalyl chloride or EDC and HOBT.
| 【1】 Patel, S.A.; Staeger, M.A.; McCarty, C.M.; et al.; Discovery of inhibitors of cell adhesion molecule expression in human endothelial cells: Selective inhibition of ICAM-1 and E-selectin expression. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 74. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (III) | 25437 | 4-methylphenylhydrosulfide | 106-45-6 | C7H8S | 详情 | 详情 |
| (IV) | 35537 | 3-chloro-5-[(4-methylphenyl)sulfanyl]isonicotinaldehyde | C13H10ClNOS | 详情 | 详情 | |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 35538 | methyl 4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridine-2-carboxylate | C16H13NO2S2 | 详情 | 详情 | |
| (VII) | 35539 | 4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridine-2-carboxylic acid | C15H11NO2S2 | 详情 | 详情 | |
| (VIII) | 35544 | 1-[([4-[(4-methylphenyl)sulfanyl]thieno[2,3-c]pyridin-2-yl]carbonyl)oxy]-2,5-pyrrolidinedione | C19H14N2O4S2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate by means of lithium diisopropylamide (LDA) in THF gives 3,5-dichloropyridine-4-carbaldehyde (II), which is condensed with 4-chlorophenol (III) by means of potassium tert-butoxide in THF yielding 3,5-bis(4-chlorophenoxy)pyridine-4-carbaldehyde (IV). This compound, without isolation is cyclized with methyl thioglycolate (V) by means of Cs2CO3 in DMF affording 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VI), which is finally condensed with methylamine by means of NaH in DMF to obtain the target amide.
| 【1】 Arendsen, D.L.; Freeman, J.C.; Boyd, S.A.; et al.; Inhibitors of cell adhesion molecule expression in human endothelial cells: Modification of 2-position of 4-aryloxythieno [2,3-c]pyridines. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 75. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (III) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (IV) | 35541 | 3,5-bis(4-chlorophenoxy)isonicotinaldehyde | C18H11Cl2NO3 | 详情 | 详情 | |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 35542 | methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10ClNO3S | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Treatment of 3,5-dichloropyridine (I) with methyl formate (II), BuLi and diisopropyl amine (DIPA) in THF provides carboxaldehyde (III), which is converted into ester (VI) by first condensation with 4-chlorophenol (IV) by means of tBuOK in THF followed by cyclization with methyl thioglycolate (V) and Cs2CO3. Methyl ester (VI) reacts with methanolic ammonia to yield carboxamide (VII), which is then treated with trifluoroacetic anhydride (TFAA) in pyridine to furnish carbonitrile (VIII). Finally, (VIII) is converted into the desired compound by reaction with hydroxylamine hydrochloride (NH2OH·HCl) and TEA in EtOH.
| 【1】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (IV) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 35542 | methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10ClNO3S | 详情 | 详情 | |
| (VII) | 45475 | 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxamide | C14H9ClN2O2S | 详情 | 详情 | |
| (VIII) | 45476 | 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carbonitrile | C14H7ClN2OS | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(I)Lithiation of 3,5-dichloropyridine (I) using LDA in cold THF, followed by treatment with methyl formate, furnished aldehyde (II). Subsequent reaction of (II) with the potassium salt of 4-(trifluoromethyl)phenol (III) provided the diaryl ether (IV). Without isolation, (IV) was further condensed with methyl thioglycolate (V) in the presence of Cs2CO3, yielding the thienopyridine (VI). The title amide was then obtained by displacement of the methyl ester of (VI) with methylamine in the presence of NaH. Alternatively, ester (VI) was first hydrolyzed to acid (VII) and then condensed with methylamine employing EDC and HOBt.
| 【1】 Zhu, G.-D.; et al.; Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells. 2. Aryl modifications of 4-(aryloxy)theino[2,3-c]pyridines with fine-tuning at C-2 carbamides. J Med Chem 2001, 44, 21, 3469. |
| 【2】 Zhu, G.-D.; et al.; Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells: Aryl modification of 4-aryloxy thieno[2,3-C]pyridines. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 145. |
| 【3】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (III) | 35537 | 3-chloro-5-[(4-methylphenyl)sulfanyl]isonicotinaldehyde | C13H10ClNOS | 详情 | 详情 | |
| (IV) | 45654 | 3-chloro-5-[4-(trifluoromethyl)phenoxy]isonicotinaldehyde | C13H7ClF3NO2 | 详情 | 详情 | |
| (V) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VI) | 45655 | methyl 4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxylate | C16H10F3NO3S | 详情 | 详情 | |
| (VII) | 45656 | 4-[4-(trifluoromethyl)phenoxy]thieno[2,3-c]pyridine-2-carboxylic acid | C15H8F3NO3S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate (II), BuLi and DIEA in THF gives 3,5-dichloropyridine-4-carbaldehyde (III), which is treated with 4-bromophenol (IV) and potassium tert-butoxide in hot THF to yield the adduct (V). This compound, without isolation is cyclized with methyl 2-mercaptoacetate (VI) by means of Cs2CO3 to afford 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VII), which is hydrolyzed with LiOH in THF/water to provide the corresponding carboxylic acid (VIII). Finally, this compound is condensed with methylamine (IX) by means of EDC and HOBt in DMF to give the target amide. Alternatively, the target amide can also be obtained by direct reaction of methyl ester (VII) with methylamine (IX) in hot methanol in a sealed tube.
| 【1】 Zhu, G.-D.; et al.; Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells. 2. Aryl modifications of 4-(aryloxy)theino[2,3-c]pyridines with fine-tuning at C-2 carbamides. J Med Chem 2001, 44, 21, 3469. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (IV) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (V) | 52015 | 3-(4-bromophenoxy)-5-chloroisonicotinaldehyde | C12H7BrClNO2 | 详情 | 详情 | |
| (VI) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VII) | 52016 | methyl 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10BrNO3S | 详情 | 详情 | |
| (VIII) | 52017 | 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid | C14H8BrNO3S | 详情 | 详情 | |
| (IX) | 11021 | Methanamine; Methylamine | 74-89-5 | CH5N | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate (II), BuLi and DIEA in THF gives 3,5-dichloropyridine-4-carbaldehyde (III), which is treated with 4-bromophenol (IV) and potassium tert-butoxide in hot THF to yield the adduct (V). This compound, without isolation is cyclized with methyl 2-mercaptoacetate (VI) by means of Cs2CO3 to afford 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VII), which is finally treated with hot methanolic ammonia in a sealed tube to give the target amide.
| 【1】 Zhu, G.-D.; et al.; Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells. 2. Aryl modifications of 4-(aryloxy)theino[2,3-c]pyridines with fine-tuning at C-2 carbamides. J Med Chem 2001, 44, 21, 3469. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (IV) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (V) | 52015 | 3-(4-bromophenoxy)-5-chloroisonicotinaldehyde | C12H7BrClNO2 | 详情 | 详情 | |
| (VI) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VII) | 52016 | methyl 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10BrNO3S | 详情 | 详情 |
合成路线8
该中间体在本合成路线中的序号：(I)Preparation of 2-cyano-3,5-dichloropyridine (IV) has been reported by two alternative procedures: 3,5-Dichloropyridine (I) was converted to the corresponding N-oxide (II) by treatment with peracetic acid. Addition of cyanotrimethylsilane in the presence of dimethylcarbamoyl chloride gave rise to the cyanopyridine (IV). In a different method, displacement of the 2-chloro group of 2,3,5-trichloropyridine (III) with cuprous cyanide in refluxing diglyme led to the target nitrile (IV). Displacement of both chloro groups of pyridine (IV) by KF in hot DMSO furnished the difluoropyridine (V). The cyano group of (V) was then converted to the key amidine (VII) by two related routes. Addition of hydroxylamine to nitrile (V) provided the hydroxyamidine (VI), which was further reduced to amidine (VII) by catalytic hydrogenation. Alternatively, nitrile (V) was directly converted to (VII) by treatment with ammonium chloride and trimethylaluminium.
| 【2】 Paessens, A.; Stoltefuss, J.; Goldmann, S.; Niewohner, U.; Kramer, T.; Schlemmer, K.-H.; Weber, O.; Graef, E.; Lottmann, S.; Stolting, J.; Deres, K. (Bayer AG); Dihydropyrimidines and their use in the treatment of hepatitis B. WO 0058302 . |
| 【1】 Goldmann, S.; et al.; BAY 41-4109: A novel non-nucleosidic and highly potent inhibitor of human hepatitis B virus. Part 1: Synthesis and structure activity relationship (SAR). 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-1664. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 55042 | 3,5-dichloro-1-pyridiniumolate | C5H3Cl2NO | 详情 | 详情 | |
| (III) | 55043 | 2,3,5-Trichloropyridine | 16063-70-0 | C5H2Cl3N | 详情 | 详情 |
| (IV) | 55044 | 3,5-dichloro-2-pyridinecarbonitrile | C6H2Cl2N2 | 详情 | 详情 | |
| (V) | 55045 | 3,5-difluoro-2-pyridinecarbonitrile | C6H2F2N2 | 详情 | 详情 | |
| (VI) | 55046 | 3,5-difluoro-2-pyridinecarboximidamide | C6H5F2N3 | 详情 | 详情 | |
| (VII) | 55047 | 3,5-difluoro-N'-hydroxy-2-pyridinecarboximidamide | C6H5F2N3O | 详情 | 详情 |
合成路线9
该中间体在本合成路线中的序号：(I)The formylation of 3,5-dichloropyridine (I) with methyl formate (II), BuLi and DIEA in THF gives 3,5-dichloropyridine-4-carbaldehyde (III), which is treated with 4-bromophenol (IV) and potassium tert-butoxide in hot THF to yield the adduct (V). This compound, without isolation is cyclized with methyl 2-mercaptoacetate (VI) by means of Cs2CO3 to afford 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid methyl ester (VII), which is hydrolyzed with LiOH in THF/water to provide the corresponding carboxylic acid (VIII). Finally, this compound is condensed with ethanolamine (IX) by means of EDC and HOBt in DMF to give the target ethanolamide. Alternatively, the target amide can also be obtained by direct reaction of methyl ester (VII) with ethanolamine (IX) in refluxing methanol.
| 【1】 Zhu, G.-D.; et al.; Selective inhibition of ICAM-1 and E-selectin expression in human endothelial cells. 2. Aryl modifications of 4-(aryloxy)theino[2,3-c]pyridines with fine-tuning at C-2 carbamides. J Med Chem 2001, 44, 21, 3469. |
| 【2】 Lartey, K.; Gunawardana, I.W.; Stout, D.M.; Bhatia, P.; Patel, M.V.; Staeger, M.A.; Boyd, S.A.; Mort, N.A.; Zhu, G.-D.; McCarty, C.M.; Stewart, A.O.; Arendsen, D.L.; Condroski, K.R.; Freeman, J.C. (Abbott Laboratories Inc.); Cell adhesion-inhibiting antiinflammatory cpds.. WO 9962908 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35535 | 3,5-dichloropyridine | 2457-47-8 | C5H3Cl2N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 35536 | 3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde | 136590-83-5 | C6H3Cl2NO | 详情 | 详情 |
| (IV) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
| (V) | 52015 | 3-(4-bromophenoxy)-5-chloroisonicotinaldehyde | C12H7BrClNO2 | 详情 | 详情 | |
| (VI) | 18838 | methyl 2-sulfanylacetate | 2365-48-2 | C3H6O2S | 详情 | 详情 |
| (VII) | 52016 | methyl 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylate | C15H10BrNO3S | 详情 | 详情 | |
| (VIII) | 52017 | 4-(4-bromophenoxy)thieno[2,3-c]pyridine-2-carboxylic acid | C14H8BrNO3S | 详情 | 详情 | |
| (IX) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |