6-Methoxy-3-pyridinylamine → HCID 43427281, compound

HRID 633116Notes

Reaction equation

HRID 633116 reaction equation
COC(C1C=CC(C(O)=O)=NC=1)=O.COC1N=CC(N)=CC=1.[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([NH:31][C:32]([C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40]C)=[O:39])=[CH:36][N:35]=2)=[O:33])=[CH:27][CH:26]=1>>[CH3:23][O:24][C:25]1[N:30]=[CH:29][C:28]([NH:31][C:32]([C:34]2[CH:43]=[CH:42][C:37]([C:38]([OH:40])=[O:39])=[CH:36][N:35]=2)=[O:33])=[CH:27][CH:26]=1

Participants

4

Reactant 3

HCID 811216-Methoxy-3-pyridinylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 31941802HCID 31941802, compound

Product 1

HCID 43427281HCID 43427281, 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)+.

Sources & evidence

ORD record
ord-c5af99f5089c4cdc959a006329c6a90d
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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