4-Methyl-2-oxovaleric acid → HCID 19104945, compound

HRID 1197795Notes

Reaction equation

HRID 1197795 reaction equation
[NH2:1][CH2:2][C:3]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[CH3:16][CH:17]([CH3:24])[CH2:18][C:19](=[O:23])[C:20](O)=[O:21]>>[CH2:8]([O:7][C:3]([O:4][CH2:5][CH3:6])([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:2][NH:1][C:20](=[O:21])[C:19](=[O:23])[CH2:18][CH:17]([CH3:24])[CH3:16])[CH3:9]

Participants

3

Reactant 2

HCID 704-Methyl-2-oxovaleric acidHCID 10987537β,β-Diethoxy-3-pyridineethanamine

Product 1

HCID 19104945HCID 19104945, compound

Procedure

In a manner analogous to Example 1, by condensing 3-(2-amino-1,1-diethoxyethyl)pyridine with 4-methyl-2-oxo-pentanoic acid there is obtained N-(2,2-diethoxy-2-(3-pyridyl)ethyl]-4-methyl2-oxovaleramide as a colorless, amorphous solid. Acidic hydrolysis yields 4-methyl-N-(nicotinoylmethyl)-2-oxovaleramide and subsequent ring closure yields 3-isobutyl-5-(3-pyridyl)-2(1H)-pyrazinone as a crystalline solid, melting point 195°-196° (from ethyl acetate). The conversion into the corresponding chloride, 2-chloro-3-isobutyl-5-(3-pyridyl)pyrazine, is also effected analogously to Example 1.

Sources & evidence

ORD record
ord-44c66bc4b5be4d1790e645ce19b3640a
Source dataset
uspto-grants-1994_01
Patent number
US05278161

Reaction notes

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