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

HRID 2044169Notes

Reaction equation

HRID 2044169 reaction equation
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

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 21226206Ethyl acetate hexaneHCID 594873026-fluoro-2-(3-phenylpropylthio)-N-(thiophen-2-ylmethyl)pyridine-3-carboxylic acid amide2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-381053a8d3cd4d5bbca4f13ec9c0d2dc
Source dataset
uspto-grants-2013_11
Patent number
US08586755B2

Reaction notes

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