Dichloromethane → 5-(Trifluoromethyl)-1,3-dihydro-2H-imidazo[4,5-B]pyridin-2-one
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[C:7]([NH2:9])[C:6]([NH2:10])=[CH:5][CH:4]=1.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:15](=[O:16])C1.ClCCl>CC#N>[F:12][C:2]([F:1])([F:11])[C:3]1[N:8]=[C:7]2[NH:9][C:15](=[O:16])[NH:10][C:6]2=[CH:5][CH:4]=1Participants
5
Procedure
A mixture of the pyridine-2,3-diamine (160 mg, 0.9 mmol) from step (b) above and N,N′-disuccinimidyl carbonate (250 mg, 0.9 mmol, Aldrich) in MeCN (5 mL) was stirred at room temperature for 13 h. Another batch of N,N′-disuccinimidyl carbonate (125 mg, 0.5 mmol, Aldrich) was added and the reaction mixture was heated at 75° C. for 90 min. The reaction mixture was cooled to room temperature and dichloromethane (20 mL) was added. The precipitate was filtered and dried under vacuo to give the title compound, which was used in the next step without additional purification. MS (ESI, pos. ion) m/z: 204 (M+1).
Workup
- temperaturethe reaction mixture was heated at 75° C. for 90 min
- temperatureThe reaction mixture was cooled to room temperature
- filtrationThe precipitate was filtered
- customdried under vacuo
Sources & evidence
- ORD record
- ord-721e84a5571c48f7aafe09f2ca09c33a
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582761B2
Reaction notes
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