Potassium Carbonate → 2-(3-phenyl-propylsulfanyl)-6-pyrrolidin-1-yl-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide

HRID 2044169노트

반응식

HRID 2044169 반응식
C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.F[C:13]1[N:18]=[C:17]([S:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]([C:29]([NH:31][CH2:32][C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[O:30])=[CH:15][CH:14]=1.CCCCCC.CC(=O)OCC>CN(C=O)C>[C:23]1([CH2:22][CH2:21][CH2:20][S:19][C:17]2[C:16]([C:29]([NH:31][CH2:32][C:33]3[S:34][CH:35]=[CH:36][CH:37]=3)=[O:30])=[CH:15][CH:14]=[C:13]([N:7]3[CH2:11][CH2:10][CH2:9][CH2:8]3)[N:18]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 21226206Ethyl acetate hexaneHCID 594873026-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)pyridine-3-carboxylic acid amide2회

생성물 1

HCID 594872982-(3-phenyl-propylsulfanyl)-6-pyrrolidin-1-yl-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

153 mg of K2CO3 and 71 mg (1.0 mmol) of pyrrolidine were added to a solution of 387 mg (1.0 mmol) of 6-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)-pyridine-3-carboxylic acid amide (exemplary compound 225) in DMF (10 ml), and the mixture was stirred for 2 h at RT. Dilution with water and extraction with EA were then carried out. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 308 mg (0.7 mmol, 71%) of 2-(3-phenyl-propylsulfanyl)-6-pyrrolidin-1-yl-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide. MS: m/z 438.2 [M+H]+.

후처리

  1. extractionDilution with water and extraction with EA
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-381053a8d3cd4d5bbca4f13ec9c0d2dc
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586755B2

반응 노트

불러오는 중…