4-Fluorobenzenesulfonyl chloride → 1-(4-Fluorobenzenesulfonyl)piperidine-4-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

HRID 2426677Notes

Reaction equation

HRID 2426677 reaction equation
[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1>CN1CCCC1=O>[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([CH:17]3[CH2:22][CH2:21][N:20]([S:37]([C:34]4[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=4)(=[O:39])=[O:38])[CH2:19][CH2:18]3)=[O:16])=[CH:12][CH:13]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 67147939Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Product 1

HCID 588676031-(4-Fluorobenzenesulfonyl)piperidine-4-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Piperidine-4-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide (70 mg) dissolved in N-methylpyrrolidone (2 ml) was mixed with potassium carbonate (45 mg) and 4-fluorobenzenesulfonyl chloride (40 mg). After 12 hours, the mixture was filtered and the filtrate was purified by preparative HPLC. This resulted in the product with the molecular weight of 474.60 (C24H31FN4O3S); MS (ESI): 475 (M+H+).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was purified by preparative HPLC
  3. customThis resulted in the product with the molecular weight of 474.60 (C24H31FN4O3S)

Sources & evidence

ORD record
ord-3c4168574a1a46c89eb723af98e2e1fd
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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