Chloroform → Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate

HRID 963066

반응식

HRID 963066 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH3:18])[S:17][C:13]=2[N:12]2[C:19]([CH3:22])=[N:20][N:21]=[C:11]2[CH2:10][N:9]=1.C(Cl)(Cl)Cl.C(=O)([O-])[OH:28].[Na+].[CH2:32]([O:34][C:35]([CH2:37][N:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[C:39]1[C:47](Cl)=[O:48])=[O:36])[CH3:33]>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:14]1[CH:15]=[C:16]([CH3:18])[S:17][C:13]=1[N:12]1[C:19]([CH3:22])=[N:20][N:21]=[C:11]1[CH2:10][NH:9][C:47]([C:39]1[N:38]([CH2:37][C:35]([O:34][CH2:32][CH3:33])=[O:36])[C:46]2[C:41]([CH:40]=1)=[CH:42][CH:43]=[CH:44][CH:45]=2)=[O:48])=[O:28]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 124343244-(2-Chlorophenyl)-2,9-dimethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepineHCID 190851631-Ethoxycarbonylmethylindole-2-carbonyl chloride

생성물 1

HCID 22439218Ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate수율 85.7%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

반응 조건

온도
60 °C

실험 절차

4-(2-Chlorophenyl)-2,9-dimethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine (4.15 g) was dissolved in 5% hydrochloric acid (50 ml), and the solution was stirred at 60° C. for 4 hours. The reaction mixture was cooled in a water bath, and chloroform (60 ml) and sodium hydrogencarbonate (12.6 g) were added with vigorous stirring. Then, 1-ethoxycarbonylmethylindole-2-carbonyl chloride (3.52 g) was added, and the mixture was stirred for 1 hour. The chloroform layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate and methanol as eluent and crystallized from a mixed solvent of ethyl acetate and hexane to give 6.23 g of ethyl 2-(4-(3-(2-chlorobenzoyl)-5-methylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-ylmethylcarbamoyl)indole-1-acetate.

후처리

  1. temperatureThe reaction mixture was cooled in a water bath
  2. stirringthe mixture was stirred for 1 hour
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography
  7. customcrystallized from a mixed solvent of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-0b71b69418774cd3a9613a0c3385e719
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760032

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