Acetyl chloride → (2S,4R)-N-(1-{4-[3-(4-acetyl-piperazin-1-yl)-propoxy]-benzoyl}-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-N-(4-chloro-phenyl)-acetamide

HRID 1786061ノート

反応式

HRID 1786061 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:39])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[CH:25][CH:24]=3)[C@@H:14]([CH3:40])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[C:41](Cl)(=[O:43])[CH3:42].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:41]([N:36]1[CH2:35][CH2:34][N:33]([CH2:32][CH2:31][CH2:30][O:29][C:26]2[CH:27]=[CH:28][C:23]([C:22]([N:15]3[C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@H:12]([N:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[C:9](=[O:11])[CH3:10])[CH2:13][C@@H:14]3[CH3:40])=[O:39])=[CH:24][CH:25]=2)[CH2:38][CH2:37]1)(=[O:43])[CH3:42]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 57595444(2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(3-piperazin-1-yl-propoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

生成物 1

HCID 57595401(2S,4R)-N-(1-{4-[3-(4-acetyl-piperazin-1-yl)-propoxy]-benzoyl}-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-N-(4-chloro-phenyl)-acetamide収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(2S,4R)-N-(4-Chloro-phenyl)-N-{2-methyl-1-[4-(3-piperazin-1-yl-propoxy)-benzoyl]-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide (168 mg) was dissolved in CH2Cl2 (2 mL). Acetic chloride (47 mg) and DIEA (52 uL) were added. The reaction mixture was stirred at room temperature overnight. The organic phase was washed with sat. NaHCO3 (2×5 mL), dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc) to afford pure (2S,4R)-N-(1-{4-[3-(4-acetyl-piperazin-1-yl)-propoxy]-benzoyl}-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl)-N-(4-chloro-phenyl)-acetamide (100 mg, 57%).

後処理

  1. washThe organic phase was washed with sat. NaHCO3 (2×5 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (EtOAc)

出典と根拠

ORDレコード
ord-a0f4868cd4cc4314a16ced02e1dfbba8
出典データセット
uspto-grants-2009_03
特許番号
US07504508B2

反応ノート

読み込み中…