(2,4-Dimethoxy-phenyl)-acetyl chloride → 2-(2,4-dimethoxy-phenyl)-N-{4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide

HRID 507411

반응식

HRID 507411 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[C:11]2[CH3:28])=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40][C:41](Cl)=[O:42]>>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[CH2:40][C:41]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:29])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]=[C:11]2[CH3:28])=[CH:6][CH:7]=1)=[O:42]

참가 물질

3

반응물 2

HCID 23083403(2,4-Dimethoxy-phenyl)-acetyl chlorideHCID 684681843-[2-(4-Amino-phenyl)-2-oxo-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one

생성물 1

HCID 252556642-(2,4-dimethoxy-phenyl)-N-{4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide

실험 절차

Synthesis in analogy to Example 8 starting from 3-[2-(4-amino-phenyl)-2-oxo-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one and (2,4-dimethoxy-phenyl)-acetyl chloride to yield 2-(2,4-dimethoxy-phenyl)-N-{4-[2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-acetamide (55 mg, 0.098 mmol) which is dissolved 5 mL dry ethanol. Subsequently LiBH4 (22.5 mg, 0.98 mmol) is added and the reaction mixture is stirred for 4 hour at reflux temperature. The reaction is then diluted with 5 mL water and the solvents evaporated. The residue is purified by preparative HPLC (method 3) to yield 2-(2,4-dimethoxy-phenyl)-N-{4-[1-hydroxy-2-(2-methyl-5-oxo-4,4-diphenyl-4,5-dihydro-imidazol-1-yl)-ethyl]-phenyl}-acetamide (15 mg, 27%). LC/MS at 254 nm; [M+H] 565; Rt=3.006 min.

출처 및 근거

ORD 기록
ord-583bfc4d328a479b9ef50c2a3ae2c9af
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786155B2

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