Isopropylamine → HCID 43427173, compound

HRID 922957Notes

Reaction equation

HRID 922957 reaction equation
COC(C1C=CC(C(O)=O)=NC=1)=O.C(N)(C)C.[CH:18]([NH:21][C:22]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][N:25]=1)=[O:23])([CH3:20])[CH3:19]>>[CH:18]([NH:21][C:22]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][N:25]=1)=[O:23])([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 6363IsopropylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 31670438HCID 31670438, compound

Product 1

HCID 43427173HCID 43427173, 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)+.

Sources & evidence

ORD record
ord-00f5d425ae9648b69bda60a7a9be237e
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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