4-Amino-1,2-dihydropyridin-2-one → HCID 68599096, compound

HRID 2170958Notes

Reaction equation

HRID 2170958 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[NH2:13][C:14]1[CH:19]=[CH:18][NH:17][C:16](=[O:20])[CH:15]=1.O=[C:22]([CH3:31])[CH2:23][C:24]([O:26][CH2:27][CH2:28][C:29]#[N:30])=[O:25]>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:15]3[C:16](=[O:20])[NH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:22]([CH3:31])=[C:23]2[C:24]([O:26][CH2:27][CH2:28][C:29]#[N:30])=[O:25])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 68599096HCID 68599096, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

14.63 g (90.81 mmol) of the compound from Example 10A, 10.00 g (90.81 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 15.65 g (90.81 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)] are dissolved in 300 ml of isopropanol and stirred at the reflux temperature under argon for 3 days. The mixture is then concentrated and subsequently purified by column chromatography (silica gel; mobile phase: initially ethyl acetate and then dichloromethane/methanol 10:1). The resulting product fractions are concentrated and then taken up in a little ethyl acetate. The precipitated product is filtered off and dried at 40° C. in vacuo overnight. 10.11 g (27% of theory) of the title compound are obtained.

Workup

  1. concentrationThe mixture is then concentrated
  2. customsubsequently purified by column chromatography (silica gel
  3. concentrationThe resulting product fractions are concentrated
  4. filtrationThe precipitated product is filtered off
  5. customdried at 40° C. in vacuo overnight

Sources & evidence

ORD record
ord-c8b4ed225687442bbfe2a5d60bb82a0c
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

Loading…