Dimethylamine → Pyrazolo(1,5-a)pyridine-3-carboxamide, N,N-dimethyl-
Reaction equation
[CH3:1][NH:2][CH3:3].[N:4]1[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[C:6]([C:13](Cl)=[O:14])[CH:5]=1>C(O)C.ClCCl>[CH3:1][N:2]([CH3:3])[C:13]([C:6]1[CH:5]=[N:4][N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=12)=[O:14]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of dimethylamine in ethanol (35% w/v; 300 ml) was added to dichloromethane (1100 ml) and the resulting solution was stirred at 0° C. and treated slowly with a solution of pyrazolo[1,5-a]pyridine-3-carbonyl chloride (61.0 g) in dry dichloromethane (1100 ml). When the addition was complete, the mixture was allowed to warm up to room temperature and stand at room temperature overnight. The mixture was then washed twice with water and the organic solution was then dried over sodium sulphate and evaporated under reduced pressure. The resulting brown oil was recrystallised from cyclohexane, to give 3-(N,N-dimethylcarbamoyl)pyrazolo[1,5-a]pyridine (42.0 g), m.p. 86°-87° C.
Workup
- additionWhen the addition
- temperatureto warm up to room temperature
- washThe mixture was then washed twice with water
- dry with materialthe organic solution was then dried over sodium sulphate
- customevaporated under reduced pressure
- customThe resulting brown oil was recrystallised from cyclohexane
Sources & evidence
- ORD record
- ord-bcecaf4fc5984c37b89eb04df6ee1bae
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04604400
Reaction notes
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