Triethylamine → 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N'-(2-chloroacetyl)hydrazide

HRID 644075ノート

反応式

HRID 644075 の反応式
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19](O)=[O:20])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[Cl:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31].C(N(CC)CC)C>ClCCl>[Cl:28][CH2:29][C:30]([NH:32][NH:33][C:19]([C:10]1[C:11]2[C:16](=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:9]=1)=[O:20])=[O:31]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 101883Chloroacetyl hydrazineHCID 686950531-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

生成物 1

HCID 686955621-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N'-(2-chloroacetyl)hydrazide収率 30.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid (1.0 g, 3.48 mmol) in dichloromethane (20 ml) was added oxalyl chloride (0.6 ml, 6.96 mmol) and the reaction stirred for 3.5 h. The solvent was evaporated under reduced pressure and the resulting residue redissolved in dichloromethane (20 ml). To the solution was added chloroacetic acid hydrazide (1.3 g, 8.97 mmol) and triethylamine (2.9 ml, 20.9 mmol) and the reaction mixture stirred for 4 h and then left to stand overnight. The solvent was evaporated under reduced pressure and the resulting residue purified by flash column chromatography eluting with 50-100% (v/v) ethyl acetate in heptane to give 1-cyclohexylmethyl-7-methoxy-1H-indole-3-carboxylic acid N′-(2-chloroacetyl)hydrazide (397 mg, 1.05 mmol).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe resulting residue redissolved in dichloromethane (20 ml)
  3. stirringthe reaction mixture stirred for 4 h
  4. waitleft
  5. waitto stand overnight
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue purified by flash column chromatography
  8. washeluting with 50-100% (v/v) ethyl acetate in heptane

出典と根拠

ORDレコード
ord-7bbb6a21e680484fbec7fbb9d71cbee2
出典データセット
uspto-grants-2010_04
特許番号
US07700634B2

反応ノート

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