5-Amino-2-methylpyridine → 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one

HRID 227009

Reaction equation

HRID 227009 reaction equation
CO[C:3](=[O:20])[C:4]([C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)=[CH:5]OCC.[CH3:21][C:22]1[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([C:4]2[C:3](=[O:20])[C:26]3[C:25](=[CH:24][CH:23]=[C:22]([CH3:21])[N:27]=3)[NH:28][CH:5]=2)=[O:19])=[CH:11][C:12]=1[CH3:18]

Participants

4

Reactant 2

HCID 2433135-Amino-2-methylpyridineHCID 668786263-Ethoxy-2-(4-methoxy-3-methyl-benzoyl)-acrylic acid methyl ester

Product 1

HCID 577547063-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-oneYield 56.9%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Experimental conditions analogous to those described for Step 1 of Example 1 were used with 0.50 g (1.88 mmol) of 3-ethoxy-2-(4-methoxy-3-methyl-benzoyl)-acrylic acid methyl ester, 0.20 g (1.88 mmol) of 6-Methyl-pyridin-3-ylamine, and 10 mL of diphenyl ether to yield 0.33 g of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one.

Sources & evidence

ORD record
ord-2b9834e73ab544c49c9d92747a0ce5c9
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Linked notes

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