Potassium Carbonate → methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate

HRID 2401287노트

반응식

HRID 2401287 반응식
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[N:10]([CH2:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)=[O:18])[C:9]2=[O:30])=[CH:4][CH:3]=1.[C:31](=[O:34])([O-])[O-:32].[K+].[K+].[C:37](=O)([O-])O.[Na+]>CN(C=O)C.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:30]=[C:9]1[N:10]([CH2:16][C:17](=[O:18])[NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C@@H:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][N:8]1[C:5]1[CH:4]=[CH:3][C:2]([C:31]([O:32][CH3:37])=[O:34])=[N:7][CH:6]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86705191HCID 86705191, 화합물

생성물 1

HCID 86705194methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 19794673N,N-dimethylformamide ethanol용매

반응 조건

온도
80 °C

실험 절차

A suspension of 2-[(5S)-3-(6-bromopyridin-3-yl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]-N-[3-(trifluoromethyl)phenyl]acetamide (100 mg), potassium carbonate (43 mg), and Pd(PPh3)4 (24 mg) in DMF/ethanol (2:1, 2.1 mL) was stirred under atmosphere of carbon monoxide gas at 80° C. for 1.5 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, the mixture was washed with ethyl acetate, and the organic layer was washed with water and brine. After concentration under reduced pressure, the residue was purified by preparative HPLC to afford methyl 5-[(4S)-2-oxo-3-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino]ethyl)-4-(propan-2-yl)imidazolidin-1-yl}pyridine-2-carboxylate (50 mg).

후처리

  1. washthe mixture was washed with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-33a956c87018456d8287f13888362968
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796272B2

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