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 2401287ノート

反応式

HRID 2401287 の反応式
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

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86705191HCID 86705191、化合物

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 19794673N,N-dimethylformamide ethanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33a956c87018456d8287f13888362968
出典データセット
uspto-grants-2014_08
特許番号
US08796272B2

反応ノート

読み込み中…