Pyrrolidine → 2'-Methyl-5'-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1'-biphenyl-4-carboxylic acid

HRID 351289Notes

Reaction equation

HRID 351289 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][N:26]=1)[C:5]([NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:23])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=2)[CH:13]=1)=[O:6].[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH3:23][C:11]1[CH:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:24]=[CH:25][N:26]=[C:2]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH:3]=2)=[CH:13][C:12]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 210905805'-[(2-Chloroisonicotinoyl)amino]-2'-methyl-1,1'-biphenyl-4-carboxylic acid

Product 1

HCID 113501482'-Methyl-5'-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1'-biphenyl-4-carboxylic acidYield 83%

Procedure

5′-[(2-Chloroisonicotinoyl)amino]-2′-methyl-1,1′-biphenyl-4-carboxylic acid (600 mg, 1.64 mmol) and pyrrolidine (0.6 ml) were heated in a sealed tube at 90° C. for 5 h. The excess pyrrolidine was evaporated under vacuum and the residue purified by flash chromatography (silica) eluting with DCM/ethanol/ammonia (20:8:1). The solvents were evaportated under vacuum to give 2′-methyl-5′-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1′-biphenyl-4-carboxylic acid (546 mg, 83%).

Workup

  1. customThe excess pyrrolidine was evaporated under vacuum
  2. customthe residue purified by flash chromatography (silica)
  3. washeluting with DCM/ethanol/ammonia (20:8:1)

Sources & evidence

ORD record
ord-b18dd4dcf1bc4f85900a7b3189153d8a
Source dataset
uspto-grants-2007_02
Patent number
US07183297B2

Reaction notes

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