【结 构 式】 |
【分子编号】25831 【品名】2-(acetamido)-3-methoxybenzamide 【CA登记号】 |
【 分 子 式 】C10H12N2O3 【 分 子 量 】208.21696 【元素组成】C 57.69% H 5.81% N 13.45% O 23.05% |
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:(VI)In an alternative procedure, 3-methoxy-2-nitrobenzoic acid (II) was treated with SOCl2 in the presence of DMF in THF, and the resulting acid chloride (III) was converted to amide (IV) with aqueous ammonia. Catalytic hydrogenation of (IV) over Pd/C produced aniline (V), which was then acetylated with AcCl and pyridine. The crude acetylamino compound (VI) was cyclized by treatment with aqueous NaOH to yield the quinazolinone (VII). Finally, demethylation of the methoxy group of (VII) with BBr3 provided the required 8-hydroxyquinazolinone.
【1】 Griffin, R.J.; Srinivasan, S.; Bowman, K.; Calvert, A.H.; Curtin, N.J.; Newell, D.R.; Pemberton, L.C.; Golding, B.T.; Resistance-modifying agents. 5. Synthesis and biological properties of quinazolinone inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase (PARP). J Med Chem 1998, 41, 26, 5247. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
19273 | acetyl chloride | 75-36-5 | C2H3ClO | 详情 | 详情 | |
(II) | 25827 | 3-methoxy-2-nitrobenzoic acid | 4920-80-3 | C8H7NO5 | 详情 | 详情 |
(III) | 25828 | 3-methoxy-2-nitrobenzoyl chloride | C8H6ClNO4 | 详情 | 详情 | |
(IV) | 25829 | 3-methoxy-2-nitrobenzamide | C8H8N2O4 | 详情 | 详情 | |
(V) | 25830 | 2-amino-3-methoxybenzamide | C8H10N2O2 | 详情 | 详情 | |
(VI) | 25831 | 2-(acetamido)-3-methoxybenzamide | C10H12N2O3 | 详情 | 详情 | |
(VII) | 25832 | 8-methoxy-2-methyl-4(3H)-quinazolinone | C10H10N2O2 | 详情 | 详情 |
Extended Information