4-Chloro-3-(pyridin-2-yl)aniline → HCID 86635785, compound

HRID 922964Notes

Reaction equation

HRID 922964 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C([NH:22][C:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][N:26]=1)=[O:24])C1C=CC=CC=1>>[CH2:9]([C:33]1[C:25]([C:23]([NH2:22])=[O:24])=[N:26][CH:27]=[C:28]([C:29]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[CH:4]=2)=[O:31])[CH:32]=1)[C:3]1[CH:4]=[CH:5][CH:7]=[CH:8][CH:2]=1

Participants

3

Reactant 2

HCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 43427193HCID 43427193, compound

Product 1

HCID 86635785HCID 86635785, compound

Procedure

250 mg of 5-(methoxycarbonyl)picolinic acid was coupled to benzylamine via Procedure G. Crude methyl 6-(benzylcarbamoyl)nicotinate was hydrolyzed via Procedure M to yield 300 mg of 6-(benzylcarbamoyl)nicotinic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 6-(benzylcarbamoyl)nicotinic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield-benzyl-N5-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-2,5-dicarboxamide. MS (Q1) 443.1 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-76705f2536bc43fc9f83396da4e6405c
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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