2-Chloronicotinic acid → ASLAN003

HRID 1909350Notes

Reaction equation

HRID 1909350 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[NH2:8].Cl[C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22]>>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[CH:5]=[C:6]([F:9])[C:7]=1[NH:8][C:19]1[N:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22]

Participants

3

Reactant 2

HCID 762582-Chloronicotinic acidHCID 533754393,5-Difluoro-3′-methoxy[1,1′-biphenyl]-4-amine2×

Product 1

HCID 24986824ASLAN003

Procedure

In another embodiment (step c2), the aminium salt of 3,5-difluoro-3′-methoxybiphenyl-4-amine from step b) is optionally, dried or semidried to remove or partially remove the solvent. Subsequently, said aminium salt is hydrolyzed in the presence of water under well-known reaction conditions to 3,5-difluoro-3′-methoxybiphenyl-4-amine and finally, 3,5-difluoro-3′-methoxybiphenyl-4-amine in the amine form is reacted with 2-chloronicotinic acid to obtain 2-[(3,5-difluoro-3′-methoxy-1,1′-biphenyl-4-yl)amino]nicotinic acid.

Workup

  1. customdried
  2. customto remove
  3. custompartially remove the solvent
  4. customis hydrolyzed in the presence of water under well-known reaction conditions to 3,5-difluoro-3′-methoxybiphenyl-4-amine

Sources & evidence

ORD record
ord-8b2d71fc5c8841b8b4d2849b39113ad8
Source dataset
uspto-grants-2013_12
Patent number
US08598363B2

Reaction notes

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