Potassium Carbonate → 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxamide

HRID 1873528ノート

反応式

HRID 1873528 の反応式
[CH3:1][N:2]([CH3:15])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([NH2:14])([CH3:13])[CH2:12][CH:7]2[CH2:6]1)=[O:4].Cl[CH2:17][C:18]([N:20]1[CH2:24][C@@H:23]([F:25])[CH2:22][C@H:21]1[C:26]#[N:27])=[O:19].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C)C=O>[C:26]([C@@H:21]1[CH2:22][C@H:23]([F:25])[CH2:24][N:20]1[C:18](=[O:19])[CH2:17][NH:14][C:11]1([CH3:13])[CH2:12][CH:7]2[CH2:6][N:5]([C:3]([N:2]([CH3:1])[CH3:15])=[O:4])[CH2:9][CH:8]2[CH2:10]1)#[N:27]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 57518632(2S,4S)-1-(2-Chloroacetyl)-4-fluoropyrrolidine-2-carbonitrileHCID 686275765-Amino-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide

生成物 1

HCID 687768935-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxamide収率 58%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

5-Amino-5-methyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 12f (130 mg, 0.616 mmol), (2S,4S)-1-(2-chloroacetyl)-4-fluoropyrrolidine-2-carbonitrile 13g (117.4 mg, 0.616 mmol) and potassium carbonate (85 mg, 0.616 mmol) were dissolved in the solvent mixture of 2 mL of dichloromethane and 2 mL of N,N-dimethylformamide with stirring under nitrogen atmosphere. The reaction mixture was reacted overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure to remove N,N-dimethylformamide and dichloromethane. The resulting residue was purified by silica gel column chromatography to obtain 5-[2-((2S,4S)-2-cyano-4-fluoro-pyrrolidin-1-yl)-2-oxo-ethylamino]-N,N,5-trimethyl-hexahydro-cyclopenta[c]pyrrole-2(1H)-carboxamide 13h (0.13 g, yield 58%) as a colorless oil.

後処理

  1. customThe reaction mixture was reacted overnight at room temperature
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto remove N,N-dimethylformamide and dichloromethane
  4. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fa07c2591e1d4873a8def2ad306645ea
出典データセット
uspto-grants-2012_11
特許番号
US08304411B2

反応ノート

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