Ethenesulfonyl chloride, 2-phenyl- → (E)-2-Phenyl-ethenesulfonic acid (1-acetyl-2,3-dihydro-1H-indol-6-yl)-(1-benzyl-piperidin-4-yl)-amide

HRID 2250870ノート

反応式

HRID 2250870 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][CH2:20][N:21]3[C:24](=[O:26])[CH3:25])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([CH:33]=[CH:34][S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:24]([N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N:14]([CH:11]3[CH2:12][CH2:13][N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:9][CH2:10]3)[S:35](/[CH:34]=[CH:33]/[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:37])=[O:36])[CH:23]=2)[CH2:19][CH2:20]1)(=[O:26])[CH3:25]

参加物

4

反応物 2

HCID 107500Ethenesulfonyl chloride, 2-phenyl-HCID 27611281-Acetyl-N-(1-benzylpiperidin-4-yl)-indolin-6-amine

生成物 1

HCID 11398198(E)-2-Phenyl-ethenesulfonic acid (1-acetyl-2,3-dihydro-1H-indol-6-yl)-(1-benzyl-piperidin-4-yl)-amide収率 92.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1-[6-(1-benzyl-piperidin-4-ylamino)-2,3-dihydro-indol-1-yl]-ethanone (0.10 g, 0.29 mmol), 2-phenyl-ethenesulfonyl chloride (87 mg, 0.43 mmol), and TEA (0.08 mL, 0.57 mmol) in CH2Cl2 (5 mL) was stirred at rt for 20 h. The reaction mixture was concentrated, and the residue was purified on silica gel (60-70% EtOAc/hexanes) to afford the title compound (138 mg, 92%). 1H NMR (500 MHz, CDCl3): 8.12 (s, 1H), 7.50-7.48 (m, 2H), 7.43 (s, 1H), 7.41-7.39 (m, 3H), 7.25 (d, J=6.8 Hz, 2H), 7.20 (t, J=7.0 Hz, 3H), 7.15 (d, J=7.9 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 6.86 (d, J=15.0 Hz, 1H), 4.13 (t, J=8.0 Hz, 2H), 3.98-3.40 (m, 1H), 3.41 (s, 2H), 3.20 (t, J=8.5 Hz, 2H), 2.87 (d, J=10.5 Hz, 2H), 2.20 (s, 3H), 2.06-2.02 (m, 2H), 1.88 (d, J=10.7 Hz, 2H), 1.61-1.55 (m, 2H). MS: exact mass calculated for C30H33N3O3S, 515.22; m/z found, 516.3 [M+H]+.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified on silica gel (60-70% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-15b5e6189a304b08a968f2b662cbffb6
出典データセット
uspto-grants-2008_01
特許番号
US07317025B2

反応ノート

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