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【结 构 式】

【分子编号】43064

【品名】3-bromo-N-[2-(dimethylamino)ethyl]-11-oxo-5,11-dihydro-10lambda(5)-pyrido[2,1-b]quinazoline-6-carboxamide

【CA登记号】

【 分 子 式 】C17H19BrN4O2

【 分 子 量 】391.26762

【元素组成】C 52.19% H 4.89% Br 20.42% N 14.32% O 8.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Treatment of 4-bromophthalic anhydride (I) in MeOH with NaOMe affords methyl ester (II), which is then treated with diphenylphosphoryl azide ((PhO)2PON3) in toluene, acetone/H2O to yield a mixture of regioisomers from which derivative (III) is obtained by chromatographic separation. Condensation of (III) with 2-chloronicotinic acid (IV) in refluxing EtOH in the presence of HCl yields pyridoquinazoline acid derivative (V), which is then condensed with N,N-dimethylethylenediamine (VI) in CH2Cl2 using BOP as coupling reagent to provide (VII). Reaction of 2-bromopyridine (VIII) in Et2O with n-BuLi and trimethylborate, followed by treatment with EtOH and HOAc, gives 3-pyridinyl boronic acid (IX), which is finally coupled to (VII) in an Na2CO3 solution via a Suzuki coupling catalyzed by Pd(PPh3)4.

1 Kitchen, D.B.; Schow, S.R.; Casscles, W.T. Jr.; Discafani, C.; Trova, M.P.; Lassota, P.; Zhang, N.; Powell, D.W.; Hetero biarylpyridoquinazolinone derivatives as anticancer agents. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 59.
2 Trova, M.P.; Zhang, N. (American Cyanamid Co.); Hetero-biaryl-pyridoquinazolinone derivs. as anti-cancer agents. EP 0944628; WO 9823617 .
3 Trova, M.P.; Zhang, N. (American Cyanamid Co.); Hetero-biaryl-pyridoquinazolinone derivs. as anti-cancer agents. US 5908840 .
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) 43060 5-bromo-2-benzofuran-1,3-dione 86-90-8 C8H3BrO3 详情 详情
(II) 43061 5-bromo-2-(methoxycarbonyl)benzoic acid C9H7BrO4 详情 详情
(III) 43062 methyl 2-amino-4-bromobenzoate 135484-83-2 C8H8BrNO2 详情 详情
(IV) 28824 2-Chloropyridine-3-carboxylic acid; 2-Chloronicotinic acid 2942-59-8 C6H4ClNO2 详情 详情
(V) 43063 3-bromo-11-oxo-5,11-dihydro-10lambda(5)-pyrido[2,1-b]quinazoline-6-carboxylic acid C13H9BrN2O3 详情 详情
(VI) 14881 N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine 108-00-9 C4H12N2 详情 详情
(VII) 43064 3-bromo-N-[2-(dimethylamino)ethyl]-11-oxo-5,11-dihydro-10lambda(5)-pyrido[2,1-b]quinazoline-6-carboxamide C17H19BrN4O2 详情 详情
(VIII) 13265 3-Bromopyridine 626-55-1 C5H4BrN 详情 详情
(IX) 38825 3-pyridinylboronic acid 1692-25-7 C5H6BNO2 详情 详情
Extended Information