Pyridine → (2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (pyridin-3-yl-methyl)-amide hydrochloride

HRID 890260Notes

Reaction equation

HRID 890260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([C:23]([Cl:25])=[O:24])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][NH2:39])[CH:33]=1>ClCCl>[ClH:25].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][NH:39][C:23]([CH:11]2[CH2:10][CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:12]2[S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])=[O:24])[CH:33]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 310183-PyridinemethanamineHCID 22250428(2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic chloride

Product 1

HCID 86584366(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (pyridin-3-yl-methyl)-amide hydrochlorideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) solution of (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic chloride (764 mg, 2 mmol) in dichloromethane (30 ml) was added pyridine (0.16 ml, 2 mmol) and 3-picolylamine (0.18 ml, 1.8 mmol). The reaction mixture was stirred at room temperature for 22 h. Aqueous work-up, formation of the hydrochloride (3N MeOH/HCl) and crystallization (diethyl ether) yielded the title compound (0.69 g, yield 70%) as a white solid, m.p. 186° C. and MS: m/e=454.5 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 22 h
  2. customAqueous work-up, formation of the hydrochloride (3N MeOH/HCl) and crystallization (diethyl ether)

Sources & evidence

ORD record
ord-ec2eefb854af45959f2cbd3b842d77c0
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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