4-Chloro-3-(pyridin-2-yl)aniline → HCID 58614679, compound

HRID 1364743Notes

Reaction equation

HRID 1364743 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.[CH3:15][O:16][C:17]1[N:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][N:27]=2)=[O:25])=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:30]([C:29]2[CH:33]=[CH:34][C:26]([C:24]([NH:23][C:20]3[CH:21]=[N:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=3)=[O:25])=[N:27][CH:28]=2)=[O:31])=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

3

Reactant 2

HCID 401519254-Chloro-3-(pyridin-2-yl)anilineHCID 43427281HCID 43427281, compound

Product 1

HCID 58614679HCID 58614679, compound

Procedure

250 mg of 5-(methoxycarbonyl)picolinic acid was coupled to 6-methoxypyridin-3-amine via Procedure G. Crude methyl 6-(6-methoxypyridin-3-ylcarbamoyl)nicotinate was hydrolyzed via Procedure M to yield 196 mg of 6-(6-methoxypyridin-3-ylcarbamoyl)nicotinic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 6-(6-methoxypyridin-3-ylcarbamoyl)nicotinic acid via Procedure G. The crude product was recrystallized to yield pure N5-(4-chloro-3-(pyridin-2-yl)phenyl)-N2-(6-methoxypyridin-3-yl)pyridine-2,5-dicarboxamide. MS (Q1) 460 (M)+.

Workup

  1. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-bc60e077cfa6455498541ad12e76a3a0
Source dataset
uspto-grants-2011_02
Patent number
US07888364B2

Reaction notes

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