Dimethylamine → 3-(2-Oxo-1,2-dihydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 466012Notes

Reaction equation

[C:1]1([C:7]2[C:15]([CH:16]=[CH:17][CH:18]=[O:19])=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[C:21]([CH2:24][N+]1C=CC=CC=1)(=O)[NH2:22].CNC>CO>[O:19]=[C:18]1[CH:17]=[C:16]([C:15]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=23)[CH:24]=[CH:21][NH:22]1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylaldehyde (cis and trans mixture) (1.15 g) and 1-carbamoylmethylpyridinium chloride (0.80 g), 50% aqueous dimethylamine (0.44 g) and methanol (10 ml) was refluxed for 3 hours. The reaction mixture was evaporated in vacuo and the residue was heated for 10 minutes at 200° C. The resulting mixture was chromatographed on silica gel (80 g) with a mixture of chloroform and methanol (100:1). The fractions containing the object compound were combined and evaporated in vacuo and recrystallized from ethanol to give 3-(2-oxo-1,2-dihydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.33 g).

Workup

temperaturewas refluxed for 3 hours
customThe reaction mixture was evaporated in vacuo
customThe resulting mixture was chromatographed on silica gel (80 g) with a mixture of chloroform and methanol (100:1)
additionThe fractions containing the object compound
customevaporated in vacuo
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-39ff9bbc27a5468db683fa52ee1ed7be
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155114

Reaction notes

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