HCID 10632805, compound → HCID 58614755, compound

HRID 922960Notes

Reaction equation

HRID 922960 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:15]([NH:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][N:23]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>>[C:15]([NH:19][C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([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:27])=[CH:24][N:23]=1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

3

Reactant 2

HCID 10632805HCID 10632805, compoundHCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614755HCID 58614755, compound

Procedure

250 mg of 5-(methoxycarbonyl)picolinic acid was coupled to tert-butylamine via Procedure G. Crude methyl 6-(tert-butylcarbamoyl)nicotinate was hydrolyzed via Procedure M to yield 250 mg of 6-(tert-butylcarbamoyl)nicotinic acid. 60 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 6-(tert-butylcarbamoyl)nicotinic acid via Procedure G. The crude product was purified by reverse phase HPLC to yield N2-tert-butyl-N5-(4-chloro-3-(pyridin-2-yl)phenyl)pyridine-2,5-dicarboxamide. MS (Q1) 409 (M)+.

Workup

  1. customThe crude product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-bf490aac29a745dbb20542eb6640fabe
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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