Benzylamine → N-benzyl-5-(3,4-dichlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-2-carboxamide
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.[Cl:28][C:29]1[CH:30]=[C:31]([C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[N:39]3[N:46]=[C:47]([C:49](O)=[O:50])[CH:48]=[C:38]3[N:37]=2)[CH:32]=[CH:33][C:34]=1[Cl:35].[CH2:52]([NH2:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.C(N(CC)CC)C>O1CCCC1.C(OCC)C>[CH2:52]([NH:59][C:49]([C:47]1[CH:48]=[C:38]2[N:37]=[C:36]([C:31]3[CH:32]=[CH:33][C:34]([Cl:35])=[C:29]([Cl:28])[CH:30]=3)[CH:41]=[C:40]([C:42]([F:45])([F:43])[F:44])[N:39]2[N:46]=1)=[O:50])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate (BOP) (0.845 g, 1.91 mmol) was added to a suspension of 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.600 g, 1.59 mmol) and benzylamine (0.209 mL, 1.91 mmol) in tetrahydrofuran (25 ml) containing triethylamine (0.665 mL, 4.77 mmol). The reaction mixture was stirred overnight at room temperature, diluted with ethyl ether (25 mL) and washed with a saturated aqueous solution of sodium bicarbonate (50 mL). The organic layer was collected, concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel to give 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid benzylamide (0.665 g, 89%).
Workup
- washwashed with a saturated aqueous solution of sodium bicarbonate (50 mL)
- customThe organic layer was collected
- concentrationconcentrated under reduced pressure
- customthe crude product was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-ad52a17fa51e4b88856111c6d4ba70a8
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098335B2
Reaction notes
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