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【结 构 式】 
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【分子编号】19136 【品名】3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine 【CA登记号】591-19-5 |
【 分 子 式 】C6H6BrN 【 分 子 量 】172.02438 【元素组成】C 41.89% H 3.52% Br 46.45% N 8.14% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 2-amino-5-nitrobenzoic acid (I) with N,N-dimethylformamide dimethylacetal (II) by heating at 100 C gives the formamidine (III), which is cyclized with 3-bromoaniline (IV) in refluxing acetic acid yielding 4-(3-bromophenyl)-6-nitroquinazoline (V). The reduction of (V) with Fe and acetic acid affords the amine (VI), which is finally acylated with 2-butynoic acid by means of isobutyl chloroformate and N-methylmorpholine in THF.
| 【1】 Wissner, A.; Johnson, B.D.; Floyd, M.B. Jr.; Kitchen, D.B. (American Cyanamid Co.); 4-Aminoquinazoline EGFR inhibitors. EP 0787722; US 5760041 . |
| 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) | 23218 | 2-amino-5-nitrobenzonitrile | 17420-30-3 | C7H5N3O2 | 详情 | 详情 |
| (II) | 11984 | N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine； Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal | 4637-24-5 | C5H13NO2 | 详情 | 详情 |
| (III) | 23219 | N'-(2-cyano-4-nitrophenyl)-N,N-dimethyliminoformamide | C10H10N4O2 | 详情 | 详情 | |
| (IV) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (V) | 23221 | N-(3-bromophenyl)-N-(6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-6-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (VI) | 23222 | N(4)-(3-bromophenyl)-4,6-quinazolinediamine; N-(6-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 | |
| (VII) | 10938 | 2-Butynoic acid | 590-93-2 | C4H4O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)Reaction of 2-amino-5-nitrobenzonitrile (I) with N,N-dimethylformamide dimethylacetal at 100 C provided formamidine (II), which was cyclized with 3-bromoaniline (III) in refluxing AcOH yielding quinazoline (IV). The nitro group of (IV) was then reduced to amine (V) with iron powder and AcOH. The resulting amine (V) was finally coupled with either acryloyl chloride (VI) in pyridine or with acrylic acid (VII) in the presence of EDC.
| 【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 . |
| 【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 . |
| 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) | 23218 | 2-amino-5-nitrobenzonitrile | 17420-30-3 | C7H5N3O2 | 详情 | 详情 |
| (II) | 23219 | N'-(2-cyano-4-nitrophenyl)-N,N-dimethyliminoformamide | C10H10N4O2 | 详情 | 详情 | |
| (III) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (IV) | 23221 | N-(3-bromophenyl)-N-(6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-6-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (V) | 23222 | N(4)-(3-bromophenyl)-4,6-quinazolinediamine; N-(6-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 | |
| (VI) | 11577 | Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride | 814-68-6 | C3H3ClO | 详情 | 详情 |
| (VII) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VII)Reaction of 2-amino-5-nitrobenzonitrile (I) with N,N-dimethylformamide dimethylacetal at 100 C provided formamidine (II), which was cyclized with 3-bromoaniline (III) in refluxing AcOH yielding quinazoline (IV). The nitro group of (IV) was then reduced to amine (V) with iron powder and AcOH. The resulting amine (V) was finally coupled with either acryloyl chloride (VI) in pyridine or with acrylic acid (VII) in the presence of EDC.
| 【1】 Frank, A.; Karn, H.; Spanig, H. (Abbott GmbH & Co. KG); Production of 1-hydroxyalkyl-5-nitroimidazoles. DE 2359625; FR 2253019; GB 1481349 . |
| 【2】 Frank, A.; Dockner, T.; Karn, H. (Abbott GmbH & Co. KG); Process for the preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole of high purity. EP 0150407 . |
| 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) | 23218 | 2-amino-5-nitrobenzonitrile | 17420-30-3 | C7H5N3O2 | 详情 | 详情 |
| (II) | 23219 | N'-(2-cyano-4-nitrophenyl)-N,N-dimethyliminoformamide | C10H10N4O2 | 详情 | 详情 | |
| (III) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (IV) | 23221 | N-(3-bromophenyl)-N-(6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-6-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (V) | 23222 | N(4)-(3-bromophenyl)-4,6-quinazolinediamine; N-(6-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 | |
| (VI) | 11577 | Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride | 814-68-6 | C3H3ClO | 详情 | 详情 |
| (VII) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(II)Coupling of chloroquinazoline (I) with 3-bromoaniline (II) in refluxing isopropanol yielded anilinoquinazoline (III). The nitro group was then reduced with Fe dust and AcOH in aqueous ethanol to give amine (IV). Finally, condensation with acrylic acid (V) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF provided the target acrylamide.
| 【1】 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth f. J Med Chem 1995, 38, 18, 3482. |
| 【2】 Dobrusin, E.M.; Bridges, A.J.; Zhou, H.; Smaill, J.B.; Doherty, A.M.; Denny, W.A.; McNamara, D.J.; Showalter, H.D. (Pfizer Inc.); Irreversible inhibitors of tyrosine kinases. JP 2000508657; WO 9738983 . |
| 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) | 19135 | 4-chloro-7-nitroquinazoline | C8H4ClN3O2 | 详情 | 详情 | |
| (II) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (III) | 19137 | N-(3-bromophenyl)-N-(7-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-7-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (IV) | 19138 | N(4)-(3-bromophenyl)-4,7-quinazolinediamine; N-(7-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 | |
| (V) | 19139 | acrylic acid | 79-10-7 | C3H4O2 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(IV)Nitration of quinazolinone (I) with fuming HNO3 in H2SO4 at 100 C gave a mixture of 6-nitro and 8-nitroquinazolines, from which the desired 6-isomer was isolated by recrystallization from AcOH. Subsequent treatment with refluxing SOCl2 and a catalytic amount of DMF gave chloride (III), which was condensed with 3-bromoaniline (IV) in isopropanol to afford anilinoquinazoline (V). Reaction with sodium alkoxide (VI) in refluxing THF provided ether (VII). Then, the nitro group was reduced with Fe dust and AcOH in aqueous ethanol to give amine (VIII). Finally, condensation with acrylic acid (X) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF yielded the target acrylamide.
| 【1】 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem 1996, 39, 4, 918. |
| 【2】 Dobrusin, E.M.; Bridges, A.J.; Zhou, H.; Smaill, J.B.; Doherty, A.M.; Denny, W.A.; McNamara, D.J.; Showalter, H.D. (Pfizer Inc.); Irreversible inhibitors of tyrosine kinases. JP 2000508657; WO 9738983 . |
| 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) | 19140 | 7-fluoro-4(3H)-quinazolinone | C8H5FN2O | 详情 | 详情 | |
| (II) | 19141 | 7-fluoro-6-nitro-4(3H)-quinazolinone | C8H4FN3O3 | 详情 | 详情 | |
| (III) | 19142 | 4-chloro-7-fluoro-6-nitroquinazoline | C8H3ClFN3O2 | 详情 | 详情 | |
| (IV) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (V) | 19144 | N-(3-bromophenyl)-N-(7-fluoro-6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-7-fluoro-6-nitro-4-quinazolinamine | C14H8BrFN4O2 | 详情 | 详情 | |
| (VI) | 19145 | 3-(4-Morpholinyl)-1-propanol sodium salt | C7H14NNaO2 | 详情 | 详情 | |
| (VII) | 19146 | N-(3-bromophenyl)-7-[3-(4-morpholinyl)propoxy]-6-nitro-4-quinazolinamine; N-(3-bromophenyl)-N-[7-[3-(4-morpholinyl)propoxy]-6-nitro-4-quinazolinyl]amine | C21H22BrN5O4 | 详情 | 详情 | |
| (VIII) | 19147 | N(4)-(3-bromophenyl)-7-[3-(4-morpholinyl)propoxy]-4,6-quinazolinediamine; N-[6-amino-7-[3-(4-morpholinyl)propoxy]-4-quinazolinyl]-N-(3-bromophenyl)amine | C21H24BrN5O2 | 详情 | 详情 | |
| (IX) | 19139 | acrylic acid | 79-10-7 | C3H4O2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(XI)In an alternative method, 3-bromoaniline (XI) was reductively condensed with piperidone (V) to afford the anilino piperidine (XII). Condensation of (XII) with oxalyl chloride, followed by Friedel-Crafts cyclization, gave rise to the N-piperidinyl isatin (XIII). This was sequentially reduced to indole (XIV) with borane in THF, and then to indoline (X) using borane and trifluoroacetic acid.
| 【1】 Kimura, T.; Takahashi, K.; Matsunaga, M.; Kawano, K.; Kubota, A.; Kitazawa, N.; Okabe, T.; Ueno, K.; Komatsu, M.; Sasaki, A. (Eisai Co., Ltd.); 1,4-Substd. cyclic amine derivs.. EP 0976732; WO 9843956 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 45821 | 1-(4-fluorophenethyl)-4-piperidinone | C13H16FNO | 详情 | 详情 | |
| (X) | 45822 | 6-bromo-1-[1-(4-fluorophenethyl)-4-piperidinyl]indoline | C21H24BrFN2 | 详情 | 详情 | |
| (XI) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (XII) | 45823 | N-(3-bromophenyl)-N-[1-(4-fluorophenethyl)-4-piperidinyl]amine; N-(3-bromophenyl)-1-(4-fluorophenethyl)-4-piperidinamine | C19H22BrFN2 | 详情 | 详情 | |
| (XIII) | 45824 | 6-bromo-1-[1-(4-fluorophenethyl)-4-piperidinyl]-1H-indole-2,3-dione | C21H20BrFN2O2 | 详情 | 详情 | |
| (XIV) | 45825 | 6-bromo-1-[1-(4-fluorophenethyl)-4-piperidinyl]-1H-indole | C21H22BrFN2 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(III)5-Nitroanthranilonitrile (I) was converted into the corresponding formamidine (II) using dimethylformamide dimethyl acetal. Heating a solution of formamidine (II) and 3-bromoaniline (III) in HOAc gave the nitro quinazoline (IV). The nitro group of (IV) was then reduced with iron in HOAc to yield the intermediate amino quinazoline (V).
| 【1】 Tsou, H.-R.; et al.; 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J Med Chem 2001, 44, 17, 2719. |
| 【2】 Wissner, A.; Johnson, B.D.; Zhang, N.; Tsou, H.-R.; Hamann, P.R. (American Cyanamid Co.); Substd. quinazoline derivs. and their use as tyrosine kinase inhibitors. EP 1000039; JP 2001515071; WO 9909016 . |
| 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) | 23218 | 2-amino-5-nitrobenzonitrile | 17420-30-3 | C7H5N3O2 | 详情 | 详情 |
| (II) | 23219 | N'-(2-cyano-4-nitrophenyl)-N,N-dimethyliminoformamide | C10H10N4O2 | 详情 | 详情 | |
| (III) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (IV) | 23221 | N-(3-bromophenyl)-N-(6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-6-nitro-4-quinazolinamine | C14H9BrN4O2 | 详情 | 详情 | |
| (V) | 23222 | N(4)-(3-bromophenyl)-4,6-quinazolinediamine; N-(6-amino-4-quinazolinyl)-N-(3-bromophenyl)amine | C14H11BrN4 | 详情 | 详情 |
合成路线8
该中间体在本合成路线中的序号：(VIII)Cyclization of 4-[(3-bromophenyl)amino]-6,7-dihydroxyquinazoline (I) with ditosylate (II) [prepared by sulfonylation of triethylene glycol (III) with p-TsCl in the presence of NaOH in THF/H2O (1)] by means of K2CO3 in DMF at 80-90 °C yields the tetraoxacyclododecane derivative (IV), which is finally submitted to Sonogashira coupling with (trimethylsilyl)acetylene (V) using Pd(PPh3)4, CuI and K2CO3 in refluxing DMF .
The aryl bromide precursor (IV) can also be prepared by chlorination of the quinazolinone (VI) using POCl3 in the presence of a catalytic amount of DMF at reflux to afford the 4-chloroquinazoline derivative (VII), which is then coupled with 3-bromoaniline (VIII) in i-PrOH/DMF .
Alternatively, condensation of chloroquinazoline (VII) with 3-ethynyl-aniline (IX) in refluxing i-PrOH/DMF directly produces icotinib .
| 【1】 Wang, Y., Ding, L., Tan, F. et al. (Zhejiang Beta Pharma, Inc.). Icotinib hydrochloride, synthesis, crystallographic form, medical combination, and uses thereof. CN 10187818, EP 2392576, JP 2011527291, KR 2011031370, US 2011182882, WO 2010003313. |
| 【2】 Zhang, D., Xie, G., Davis, C., Cheng, Z., Chen, H., Wang, Y., Kamal, M.(Beta Pharma, Inc.). Fused quinazoline derivatives useful as tyrosine kinase inhibitors. US 2004048883, US 7078409, WO 2003082830. |
| 【3】 Hu, S., Xie, G., Zhang, D.X. et al. Synthesis and biological evaluation of crown ether fused quinazoline analogues as potent EGFR inhibitors. Bioorg Med Chem Lett 2012, 22(19): 6301-5. |
| 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) | 67978 | 4-[(3-bromophenyl)amino]-6,7-dihydroxyquinazoline | C14H10BrN3O2 | 详情 | 详情 | |
| (II) | 67980 | (ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate) | 19249-03-7 | C20H26O8S2 | 详情 | 详情 |
| (III) | 67979 | 2,2'-(ethane-1,2-diylbis(oxy))diethanol;Triethylene glycol | 112-27-6 | C6H14O4 | 详情 | 详情 |
| (IV) | 67981 | N-(3-bromophenyl)-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine | C20H20BrN3O4 | 详情 | 详情 | |
| (V) | 23897 | ethynyl(trimethyl)silane；trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
| (VI) | 67982 | 7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4(3H)-one | C14H16N2O5 | 详情 | 详情 | |
| (VII) | 67983 | 4-chloro-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazoline | C14H15ClN2O4 | 详情 | 详情 | |
| (VIII) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (IX) | 56445 | 3-Aminophenylacetylene; 3-Ethynylaniline; m-Aminophenylacetylene | 54060-30-9 | C8H7N | 详情 | 详情 |
合成路线9
该中间体在本合成路线中的序号：(VIII)Chlorination of 4,5-dimethoxy-2-nitrobenzoic acid (X) with SOCl2, followed by reaction with aqueous ammonia yields the nitrobenzamide (XI), which is reduced to the corresponding aminobenzamide (XII) by means of NaBH4 in the presence of catalytic amounts of CuSO4. Anthranilamide (XII) is then cyclized to quinazolinone (XIII) by refluxing in formic acid . Alternatively, cyclization of 4,5-dimethoxyanthranilic acid (XIV), either by heating with formamide at 190 °C or with formamidine hydrochloride at 210 °C , gives rise to quinazolinone (XIII) . Subsequent chlorination of compound (XIII) to the corresponding 4-chloroquinazoline (XV) is accomplished by treatment with either POCl3 , SOCl2 or (COCl)2 in the presence of catalytic amounts of DMF. Chloroquinazoline (XV) is then condensed with 3-bromoaniline (VIII) in refluxing EtOH or i-PrOH to produce anilinoquinazoline (XVI) , which is finally demethylated by either treatment with BBr3 in THF or by heating with pyridinium chloride at 205 °C .
| 【1】 Hu, S., Xie, G., Zhang, D.X. et al. Synthesis and biological evaluation of crown ether fused quinazoline analogues as potent EGFR inhibitors. Bioorg Med Chem Lett 2012, 22(19): 6301-5. |
| 【2】 Uckun, F.M., Narla, R.K., Liu, X.-P. (Parker Hughes Institute). Quinazolines for treating brain tumor. EP 1082311, JP 2002516823, US 6316454, WO 1999061428. |
| 【3】 Barker, A.J. (AstraZeneca plc). Quinazoline derivatives. CA 2086968, EP 0566226, JP 1994073025, US 5457105, US 5616582. |
| 【4】 Johnström, P., Fredriksson, A., Thorell, J.-O., Stone-Elander, S. Synthesis of [methoxy-11C]PD153035, a selective EGR receptor tyrosine kinase inhibitor. J Label Compd Radiopharm 1998, 41(7): 623-9. |
| 【5】 Bridges, A.J., Zhou, H., Cody, D.R. et al. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor. J Med Chem 1996, 39(1): 267-76. |
| 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) | 67978 | 4-[(3-bromophenyl)amino]-6,7-dihydroxyquinazoline | C14H10BrN3O2 | 详情 | 详情 | |
| (VIII) | 19136 | 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine | 591-19-5 | C6H6BrN | 详情 | 详情 |
| (X) | 31789 | 4,5-dimethoxy-2-nitrobenzoic acid | 4998-07-6 | C9H9NO6 | 详情 | 详情 |
| (XI) | 31791 | 4,5-dimethoxy-2-nitrobenzamide | 4959-60-8 | C9H10N2O5 | 详情 | 详情 |
| (XII) | 31792 | 2-amino-4,5-dimethoxybenzamide | 5004-88-6 | C9H12N2O3 | 详情 | 详情 |
| (XIII) | 18684 | 6,7-dimethoxy-4(3H)-quinazolinone | 13794-72-4 | C10H10N2O3 | 详情 | 详情 |
| (XIV) | 23763 | 2-amino-4,5-dimethoxybenzoic acid | 5653-40-7 | C9H11NO4 | 详情 | 详情 |
| (XV) | 23765 | 4-chloro-6,7-dimethoxyquinazoline; 4-chloro-6-methoxy-7-quinazolinyl methyl ether | C10H9ClN2O2 | 详情 | 详情 | |
| (XVI) | 67984 | N-(3-bromophenyl)-6,7-dimethoxyquinazolin-4-amine hydrochloride | 183322-45-4 | C16H14BrN3O2.HCl | 详情 | 详情 |