Dimethylamine → 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamide

HRID 1372392ノート

反応式

HRID 1372392 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13](O)=[O:14])[C:5]=2[C:4](=[O:16])[CH2:3]1.[C:18](N1C=CN=C1)([N:20]1C=CN=[CH:21]1)=O.CNC>ClCCl.O1CCCC1>[CH3:1][C:2]1([CH3:17])[CH2:10][C:9]2[NH:8][CH:7]=[C:6]([CH2:11][CH2:12][C:13]([N:20]([CH3:21])[CH3:18])=[O:14])[C:5]=2[C:4](=[O:16])[CH2:3]1

参加物

6

反応物 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

生成物 1

HCID 225711373-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamide収率 78%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid (1.65 g, 7 mmol) in dichloromethane (15 mL) was added 1.36 g (8.4 mmol) of carbonyldiimidazole. The mixture was stirred at room temperature until the solution became clear. To the mixture was added dimethylamine (14 mL of a 2.0M solution in tetrahydrofuran). The mixture was stirred at room temperature overnight and then concentrated. The residue was redissloved in dichloromethane, washed with brine and concentrated. The solid was washed with ethyl acetate until it became white and dried to give 1.4 g (78% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-N,N-dimethyl-propionamide. 1H-NMR (360 MHz, diemthylsulfoxide-d6) δ10.93 (br s, 1H, NH), 6.48 (s, 1H), 2.94 (s, 3H, CH3), 2.79 (s, 3H, CH3), 2.72 (m, 2H, CH2), 2.57 (s, 2H, CH2), 2.48 (m, 2H, CH2), 2.17 (s, 2H, CH2), 1.00 (m, 6H, 2×CH3). MS m/z 262 [M+].

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated
  3. washwashed with brine
  4. concentrationconcentrated
  5. washThe solid was washed with ethyl acetate until it
  6. customdried

出典と根拠

ORDレコード
ord-9b98c204ede44052a2fee3f84418ea88
出典データセット
uspto-grants-2007_01
特許番号
US07157577B2

反応ノート

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