4-Amino-4'-chlorodiphenyl → Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate

HRID 405211Notes

Reaction equation

HRID 405211 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[N:15][CH:16]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]2[CH:39]=[CH:38][C:37]([NH:40][CH2:2][C:3]3[CH:8]=[C:7]([F:9])[C:6]([F:10])=[CH:5][C:4]=3[C:11]3[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:18])=[N:15][CH:16]=3)=[CH:36][CH:35]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 86754-Amino-4'-chlorodiphenylHCID 11430Potassium CarbonateHCID 86674272Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate

Product 1

HCID 71060105Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-4,5-difluorophenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-(5-(2-(bromomethyl)-4,5-difluorophenyl)picolinamido)propanoate (115 mg, 0.27 mmol), 4′-chloro-[1,1′-biphenyl]-4-amine (110 mg, 0.54 mmol), and K2CO3 (74 mg, 0.54 mmol) were diluted with DMF (0.3 mL) and the resulting mixture was stirred at room temperature. After 2 h the resulting mixture directly purified via column chromatography to yield the title compound.

Workup

  1. customAfter 2 h the resulting mixture directly purified via column chromatography

Sources & evidence

ORD record
ord-2e1050c17f0f44d19001a2459e4b3424
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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