Water → Ethyl 1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)pyrazole-4-carboxylate

HRID 1162752

반응식

HRID 1162752 반응식
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:9]([C:13]([F:16])([F:15])[F:14])=[N:10][NH:11][CH:12]=1)=[O:7])[CH3:4].Br[CH2:18][C:19]([NH:21][C:22]1[S:26][C:25]2[CH2:27][CH2:28][CH2:29][CH2:30][C:24]=2[C:23]=1[C:31]([NH2:33])=[O:32])=[O:20].O>CN(C=O)C>[C:31]([C:23]1[C:24]2[CH2:30][CH2:29][CH2:28][CH2:27][C:25]=2[S:26][C:22]=1[NH:21][C:19](=[O:20])[CH2:18][N:11]1[CH:12]=[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])[C:9]([C:13]([F:15])([F:16])[F:14])=[N:10]1)(=[O:32])[NH2:33]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 595205232-(2-Bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 178469923HCID 178469923, 화합물

생성물 1

HCID 59520504Ethyl 1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)pyrazole-4-carboxylate수율 19%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

NaH (60% [w/w] suspension in oil, 10 mg, 0.25 mmol) was added to a solution of ethyl-3-(trifluoromethyl)pyrazole-4-carboxylate (25 mg, 0.056 mmol) in DMF (2 mL). The reaction mixture was stirred at RT for 60 min before the addition of 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide. The reaction mixture was heated at 120° C. for 10 min in the microwave. Water (5 μL) was added and the reaction mixture extracted with EtOAc (3×10 mL). The combined EtOAc layers were washed with water (5×5 mL), brine (5 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure to give the crude reaction mixture as a yellow solid (44 mg, 0.01 mmol). Purification by preparative reverse phase HPLC gave the desired product (10 mg, 0.024 mmol, 19%).

후처리

  1. extractionthe reaction mixture extracted with EtOAc (3×10 mL)
  2. washThe combined EtOAc layers were washed with water (5×5 mL), brine (5 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto give the crude
  7. customPurification by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-78999923d8344cb1ba7bb7fa70f40f16
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820707B2

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