Reaction equation
F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[N:38]3[N:45]=[C:46]([C:48]([OH:50])=O)[CH:47]=[C:37]3[N:36]=2)=[CH:31][CH:30]=1.[S:51]1[CH:55]=[CH:54][CH:53]=[C:52]1[CH2:56][NH2:57].C(N(CC)CC)C>C1COCC1.C(OCC)C>[S:51]1[CH:55]=[CH:54][CH:53]=[C:52]1[CH2:56][NH:57][C:48]([C:46]1[CH:47]=[C:37]2[N:36]=[C:35]([C:32]3[CH:33]=[CH:34][C:29]([Br:28])=[CH:30][CH:31]=3)[CH:40]=[C:39]([C:41]([F:44])([F:42])[F:43])[N:38]2[N:45]=1)=[O:50]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.144 g, 0.327 mmol) was added to a suspension of 5-(4-bromo-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.115 g, 0.298 mmol) and thiophene-2-methylamine (0.034 mL, 0.327 mmol) in THF (10 mL) containing triethylamine (0.124 mL, 0.893 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl ether (5 mL) and washed with a saturated aqueous solution of sodium bicarbonate (10 mL). The organic layer was collected, concentrated under reduced pressure and the crude product was purified by column chromatography to give 5-(4-bromo-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (thiophen-2-ylmethyl)-amide (0.105 g, 73%).
Workup
- washwashed with a saturated aqueous solution of sodium bicarbonate (10 mL)
- customThe organic layer was collected
- concentrationconcentrated under reduced pressure
- customthe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-1508177c78c54f6c8475a6029c39a750
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833371B2
Linked notes
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