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

HRID 644075노트

반응식

HRID 644075 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7bbb6a21e680484fbec7fbb9d71cbee2
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

반응 노트

불러오는 중…