Benzylamine → 5-Pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid benzylamide
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.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34]1[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[N:37]2[N:44]=[C:45]([C:47]([OH:49])=O)[CH:46]=[C:36]2[N:35]=1.[CH2:50]([NH2:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[CH2:50]([NH:57][C:47]([C:45]1[CH:46]=[C:36]2[N:35]=[C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=3)[CH:39]=[C:38]([C:40]([F:41])([F:43])[F:42])[N:37]2[N:44]=1)=[O:49])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.430 g, 0.973 mmol) was added to a suspension of 5-pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.250 g, 0.811 mmol) and benzylamine (0.106 mL, 0.973 mmol) in tetrahydrofuran (10 mL) containing triethylamine (0.339 ml, 2.43 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl ether (10 mL) and washed with a saturated aqueous solution of sodium bicarbonate (10 mL). The organic layer was collected, concentrated under reduced pressure and crude the product was purified by column chromatography on silica gel to give 5-pyridin-2-yl-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid benzylamide (0.280 g, 86%).
Workup
- washwashed with a saturated aqueous solution of sodium bicarbonate (10 mL)
- customThe organic layer was collected
- concentrationconcentrated under reduced pressure and crude the product
- customwas purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-425c76a157aa4a56aa708107dad64d02
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098335B2
Reaction notes
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