Sodium Hydroxide → N-(cyclopropylmethyl)-8-iodo-7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine
Reaction equation
[CH:1]1([CH2:4][NH:5][C:6]([NH:8][NH:9][C:10]2[C:15]([I:16])=[C:14]([CH3:17])[CH:13]=[CH:12][N:11]=2)=O)[CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>C(OCC)(=O)C>[CH:1]1([CH2:4][NH:5][C:6]2[N:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[C:15]([I:16])[C:10]3=[N:9][N:8]=2)[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A mixture of N-(cyclopropylmethyl)-2-(3-iodo-4-methylpyridin-2-yl)hydrazinecarboxamide (preparation 28c, 0.85 g, 2.5 mmol) and phosphorous oxychloride (10 mL) was stirred at 75° C. overnight. The reaction mixture was cooled to ambient temperature and added slowly to an ice-water mixture and then ethyl acetate was added. To the cooled, stirred, biphasic mixture was added aqueous sodium hydroxide solution until the aqueous layer reached a pH of 8. The organic layer was washed with water, brine, dried (MgSO4) and the solvent evaporated in vacuo to yield the title compound (0.77 g, 96%) as a pale yellow solid.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- stirringTo the cooled, stirred
- washThe organic layer was washed with water, brine
- dry with materialdried (MgSO4)
- customthe solvent evaporated in vacuo
Sources & evidence
- ORD record
- ord-e1196e7cb20c469ca38d358541194cc5
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450341B2
Reaction notes
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