4-Amino-1,2-dihydropyridin-2-one → HCID 68599964, compound

HRID 2090212Notes

Reaction equation

HRID 2090212 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.O=[C:16]([CH3:25])[CH2:17][C:18]([O:20][CH2:21][CH2:22][C:23]#[N:24])=[O:19].[NH2:26][C:27]1[CH:32]=[CH:31][NH:30][C:29](=[O:33])[CH:28]=1>CC(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[C:28]3[C:29](=[O:33])[NH:30][CH:31]=[CH:32][C:27]=3[NH:26][C:16]([CH3:25])=[C:17]2[C:18]([O:20][CH2:21][CH2:22][C:23]#[N:24])=[O:19])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 187000874-Bromo-2-(trifluoromethoxy)benzaldehyde

Product 1

HCID 68599964HCID 68599964, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10.00 g (31.17 mmol) of the compound from Example 6A and 6.41 g (31.17 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are introduced into 100 ml of 2-propanol and, after adding 4.09 g (37.17 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)], stirred at the reflux temperature for three days. After cooling, the solvent is removed under reduced pressure, and the crude product is purified by column chromatography (silica gel; mobile phase: dichloromethane/methanol 10:1). 7.38 g (36% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed under reduced pressure
  3. customthe crude product is purified by column chromatography (silica gel; mobile phase: dichloromethane/methanol 10:1)

Sources & evidence

ORD record
ord-658f3d45a84c48519c4b3e577bf55da2
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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