3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】35536

【品名】3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde

【CA登记号】136590-83-5

【分子式】C₆H₃Cl₂NO

【分子量】176.00136

【元素组成】C 40.95% H 1.72% Cl 40.29% N 7.96% O 9.09%

与该中间体有关的原料药合成路线共 9 条

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5 合成路线6 合成路线7 合成路线8 合成路线9

合成路线1

该中间体在本合成路线中的序号：(II)

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.

参考文献中间体

合成目标

【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：(II)

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.

参考文献中间体

合成目标

【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：(II)

参考文献中间体

合成目标

【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：(V)

Friedel-Crafts hydroxymethylation of 3-methoxybenzoic acid (I) using aqueous formaldehyde and HCl gave rise to 6-methoxyisobenzofuran-1-one (II). After radical bromination of (II) with N-bromosuccinimide in the presence of benzoyl peroxide, the resulting 3-bromo derivative (III) was condensed with triphenyl phosphine to afford the phosphonium salt (IV). Wittig condensation of 3,5-dichloropyridine-4-carbaldehyde (V) with the phosphonium bromide (IV) provided the 3-(pyridylmethylene)isobenzofuranone (VI). Reaction of the enol lactone function of (VI) with hydrazine produced the phthalazinone derivative (VII), which was further converted to the 4-chlorophthalazine (VIII) upon treatment with POCl3. The 4-chloro group of (VIII) was finally displaced with the sodium salt of 1,2,4-triazole (IX) to give the title compound.

参考文献中间体

合成目标

【2】 Norcini, G.; Morazzoni, G.; Leali, G.M.; Napoletano, M.; Grancini, G.; Pellacini, F. (Zambon Group SpA); Phthalazine derivs. phosphodiesterase 4 inhibitors. EP 1097142; US 6329370; WO 0005218 .
【1】 Norcini, G.; Pellacini, F.; Pradella, L.; Marchini, F.; Morazzoni, G.; Ferlenga, P.; Napoletano, M.; Phathalazine PDE4 inhibitors. Part 2: The synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives. Bioorg Med Chem Lett 2001, 11, 1, 33.

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)	28559	m-Anisic acid; 3-Methoxybenzoic acid	586-38-9	C₈H₈O₃	详情	详情
(II)	50943	6-methoxyphthalide		C₉H₈O₃	详情	详情
(III)	50944	3-bromo-6-methoxy-2-benzofuran-1(3H)-one		C₉H₇BrO₃	详情	详情
(IV)	50945	(5-methoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl)(triphenyl)phosphonium bromide		C₂₇H₂₂BrO₃P	详情	详情
(V)	35536	3,5-dichloroisonicotinaldehyde; 3,5-Dichloropyridine-4-carbaldehyde	136590-83-5	C₆H₃Cl₂NO	详情	详情
(VI)	50946	3-[(Z)-(3,5-dichloro-4-pyridinyl)methylidene]-6-methoxy-2-benzofuran-1-one		C₁₅H₉Cl₂NO₃	详情	详情
(VII)	50947	4-[(3,5-dichloro-4-pyridinyl)methyl]-7-methoxy-1(2H)-phthalazinone		C₁₅H₁₁Cl₂N₃O₂	详情	详情
(VIII)	50948	4-chloro-1-[(3,5-dichloro-4-pyridinyl)methyl]-6-methoxyphthalazine; 4-chloro-1-[(3,5-dichloro-4-pyridinyl)methyl]-6-phthalazinyl methyl ether		C₁₅H₁₀Cl₃N₃O	详情	详情
(IX)	13135	1H-1,2,4-Triazole; 1,2,4-Triazole	288-88-0	C₂H₃N₃	详情	详情

合成路线5

该中间体在本合成路线中的序号：(III)

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.

参考文献中间体

合成目标

【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6

该中间体在本合成路线中的序号：(II)

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.

参考文献中间体

合成目标

【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7

该中间体在本合成路线中的序号：(III)

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.

参考文献中间体

合成目标

【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8

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【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9

该中间体在本合成路线中的序号：(III)

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.

参考文献中间体

合成目标

【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

Extended Information