1-Chlorobutane-2,3-dione → HCID 68695579, 화합물

HRID 644039

반응식

HRID 644039 반응식
Cl[CH2:2][C:3](=O)[C:4](=[O:6])[CH3:5].[CH:8]1([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][CH3:25])[C:17]([C:26](=[S:28])[NH2:27])=[CH:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(O)C>[CH:8]1([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][CH3:25])[C:17]([C:26]3[S:28][CH:2]=[C:3]([C:4](=[O:6])[CH3:5])[N:27]=3)=[CH:16]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

참가 물질

4

반응물 2

HCID 796801-Chlorobutane-2,3-dioneHCID 86073268HCID 86073268, 화합물

생성물 1

HCID 68695579HCID 68695579, 화합물수율 75.9%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

A solution of 1-chloro-2,3-butanedione (0.717 g, 5.95 mmol) in ethanol (3 ml) was added dropwise to a solution of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide (prepared as in Example 16; 1.20 g, 3.97 mmol) in ethanol (12 ml) at room temperature, and then the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and the obtained residue was mixed with dichloromethane (50 ml) and washed sequentially with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by column chromatography eluting with 33% (v/v) ethyl acetate in n-heptane to afford 1-{2-[1-(cyclohexyl)methyl-7-methoxy-1H-indol-3-yl]thiazol-4-yl}ethanone as a brown solid (1.11 g).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe obtained residue was mixed with dichloromethane (50 ml)
  3. washwashed sequentially with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by column chromatography
  7. washeluting with 33% (v/v) ethyl acetate in n-heptane

출처 및 근거

ORD 기록
ord-c14c02b4e34441b692760fa5c8747f6c
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

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