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【结 构 式】 
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【分子编号】31637 【品名】2-[6-bromo-4-oxo-2-phenethyl-3(4H)-quinazolinyl]acetic acid 【CA登记号】 |
【 分 子 式 】C18H15BrN2O3 【 分 子 量 】387.23278 【元素组成】C 55.83% H 3.9% Br 20.63% N 7.23% O 12.4% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of 2-amino-5-bromobenzoic acid (I) with 3-phenylpropionyl chloride (II) by means of DMAP and Et3N in DMF gives the benzoxazinone (III), which by heating with glycine methyl ester (IV) yields the quinazolinone (V). The hydrolysis if (V) with NaOH in THF/water affords 2-[6-bromo-4-oxo-2-(2-phenylethyl)-3,4-dihydroquinazolin-3-yl]acetic acid (VI), which is condensed with the monoprotected hexane-1,6-diamine (VII), by means of HOBt, EDC and NMM to provide the amide (VIII). The condensation of (VIII) with phenylboronic acid (IX) by means of palladium tetrakis(triphenylphosphoine) gives the 6-phenyl substituted quinazolinone (X), which is finally deprotected with HCl.
| 【1】 Ye, Z.; Bakshi, R.K.; Gao, Y.; et al.; Modeling directed design and biological evaluation of quinazolinones as non-peptidic growth hormone secretagogues. Bioorg Med Chem Lett 2000, 10, 1, 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 |
|---|---|---|---|---|---|---|
| (A) | 16593 | Phenylboronic acid；Benzeneboronic acid;Phenylboron dihydroxide | 98-80-6 | C6H7BO2 | 详情 | 详情 |
| (I) | 31634 | 2-amino-5-bromobenzoic acid | 5794-88-7 | C7H6BrNO2 | 详情 | 详情 |
| (II) | 16240 | 3-phenylpropanoyl chloride; Hydrocinnamoylchloride | 645-45-4 | C9H9ClO | 详情 | 详情 |
| (III) | 31635 | 6-bromo-2-phenethyl-4H-3,1-benzoxazin-4-one | C16H12BrNO2 | 详情 | 详情 | |
| (IV) | 17568 | methyl 2-aminoacetate | C3H7NO2 | 详情 | 详情 | |
| (V) | 31636 | methyl 2-[6-bromo-4-oxo-2-phenethyl-3(4H)-quinazolinyl]acetate | C19H17BrN2O3 | 详情 | 详情 | |
| (VI) | 31637 | 2-[6-bromo-4-oxo-2-phenethyl-3(4H)-quinazolinyl]acetic acid | C18H15BrN2O3 | 详情 | 详情 | |
| (VII) | 31638 | tert-butyl 6-aminohexylcarbamate | 51857-17-1 | C11H24N2O2 | 详情 | 详情 |
| (VIII) | 31639 | tert-butyl 6-([2-[6-bromo-4-oxo-2-phenethyl-3(4H)-quinazolinyl]acetyl]amino)hexylcarbamate | C29H37BrN4O4 | 详情 | 详情 | |
| (IX) | 31640 | tert-butyl 6-([2-[4-oxo-2-phenethyl-6-phenyl-3(4H)-quinazolinyl]acetyl]amino)hexylcarbamate | C35H42N4O4 | 详情 | 详情 |