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

HRID 970217Notes

Reaction equation

HRID 970217 reaction equation
ClC1C=C(C=CN=1)C(NC1C=CC(C)=C(C2C=CC(C(O)=O)=CC=2)C=1)=O.[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:47])[C:36]2[CH:41]=[CH:40][N:39]=[C:38]([N:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:37]=2)=[CH:30][C:29]=1[C:48]1[CH:53]=[CH:52][C:51]([C:54]([OH:56])=[O:55])=[CH:50][CH:49]=1.N1CCCC1>>[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:47])[C:36]2[CH:41]=[CH:40][N:39]=[C:38]([N:42]3[CH2:46][CH2:45][CH2:44][CH2:43]3)[CH:37]=2)=[CH:30][C:29]=1[C:48]1[CH:49]=[CH:50][C:51]([C:54]([OH:56])=[O:55])=[CH:52][CH:53]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 865952792'-Methyl-5'-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1'-biphenyl-4-carboxylic acid 5'-[(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

2′-Methyl-5′-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1′-biphenyl-4-carboxylic acid 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 evaporated under vacuum to give 2′-methyl-5′-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1′-biphenyl-4-carboxylic acid (546 mg, 83%). LCMS: retention time 2.74 min, MH+402.

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)
  4. customThe solvents were evaporated under vacuum

Sources & evidence

ORD record
ord-1031bba06e9640808e98f1aaf03c2c73
Source dataset
uspto-grants-2007_12
Patent number
US07309800B2

Reaction notes

Loading…