4-Amino-1,2-dihydropyridin-2-one → HCID 68601724, compound

HRID 2170968Notes

Reaction equation

HRID 2170968 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[NH2:15][C:16]1[CH:21]=[CH:20][NH:19][C:18](=[O:22])[CH:17]=1.O=[C:24]([CH3:33])[CH2:25][C:26]([O:28][CH2:29][CH2:30][C:31]#[N:32])=[O:27]>C(O)C>[CH3:33][C:24]1[NH:15][C:16]2[CH:21]=[CH:20][NH:19][C:18](=[O:22])[C:17]=2[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:25]=1[C:26]([O:28][CH2:29][CH2:30][C:31]#[N:32])=[O:27]

Participants

5

Reactant 3

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 68601724HCID 68601724, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.00 g (15.94 mmol) of the compound from Example 5A, 1.75 g (15.94 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 2.47 g (15.94 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are dissolved in 60 ml of ethanol and stirred at the reflux temperature under argon overnight. The precipitated product is then filtered off, washed with ethanol and diethyl ether and dried under high vacuum. 2.30 g (35% of theory) of the title compound are obtained in the form of beige-colored crystals.

Workup

  1. filtrationThe precipitated product is then filtered off
  2. washwashed with ethanol and diethyl ether
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-7b5827fa0b6f4865b12912155f0edf50
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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