4-Amino-2-hydroxy-6-methylpyridine → 2-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate

HRID 2090203Notes

Reaction equation

HRID 2090203 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[C:8]([C:16](=O)[CH3:17])[C:9]([O:11][CH2:12][CH2:13][C:14]#[N:15])=[O:10])=[C:5]([O:21][CH3:22])[CH:4]=1)#[N:2].[NH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[NH:27][C:26](=[O:31])[CH:25]=1>CC(O)C>[C:1]([C:3]1[CH:20]=[CH:19][C:6]([CH:7]2[C:25]3[C:26](=[O:31])[NH:27][C:28]([CH3:30])=[CH:29][C:24]=3[NH:23][C:16]([CH3:17])=[C:8]2[C:9]([O:11][CH2:12][CH2:13][C:14]#[N:15])=[O:10])=[C:5]([O:21][CH3:22])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 100575014-Amino-2-hydroxy-6-methylpyridineHCID 685996632-Cyanoethyl 2-(4-cyano-2-methoxybenzylidene)-3-oxobutanoate

Product 1

HCID 686003052-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.49 g (5.00 mmol) of the compound from Example 24A are introduced into 30 ml of 2-propanol, mixed with 620 mg (5.00 mmol) of 4-amino-6-methylpyridin-2(1H)-one [Bisagni, E., Hung, N. C., Synthesis, 765-766 (1984)] and then stirred at the reflux temperature overnight. After cooling, the precipitate is filtered off, washed with diethyl ether and dried under high vacuum. 1.53 g (76% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. washwashed with diethyl ether
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-cdb7a6e0997c48a28fdfc867f1c158b5
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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