4-Amino-5-methylpyridin-2(1H)-one → 2-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2,8-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate

HRID 2090206Notes

Reaction equation

HRID 2090206 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[C:29]([CH3:30])=[CH:28][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][CH:28]=[C:29]([CH3:30])[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 132957324-Amino-5-methylpyridin-2(1H)-oneHCID 685996632-Cyanoethyl 2-(4-cyano-2-methoxybenzylidene)-3-oxobutanoate

Product 1

HCID 686008282-Cyanoethyl 4-(4-cyano-2-methoxyphenyl)-2,8-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.69 g (9.00 mmol) of the compound from Example 24A are introduced into 45 ml of 2-propanol, mixed with 1.17 g (9.00 mmol) of 4-amino-5-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. 2.22 g (61% 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-5e44aa4098f74f4baa91e3d2e311451a
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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