4-Chloro-3-(pyridin-2-yl)aniline → HCID 58614742, compound

HRID 922958Notes

Reaction equation

HRID 922958 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.[CH:15]([NH:18][C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][N:22]=1)=[O:20])([CH3:17])[CH3:16]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:25]([C:24]2[CH:28]=[CH:29][C:21]([C:19]([NH:18][CH:15]([CH3:17])[CH3:16])=[O:20])=[N:22][CH:23]=2)=[O:26])=[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 43427173HCID 43427173, compound

Product 1

HCID 58614742HCID 58614742, compound

Procedure

250 mg of 5-(methoxycarbonyl)picolinic acid was coupled to isopropylamine via Procedure G. Crude methyl 6-(isopropylcarbamoyl)nicotinate was hydrolyzed via Procedure M to yield 227 mg of 6-(isopropylcarbamoyl)nicotinic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 6-(isopropylcarbamoyl)nicotinic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield N5-(4-chloro-3-(pyridin-2-yl)phenyl)-N2-isopropylpyridine-2,5-dicarboxamide. MS (Q1) 395.1 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2eb982ac07644753a4bcc70ae1a349c1
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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