Triethylamine → (r)-n-(3-Tert-butyl-1-((tetrahydrofuran-2-yl)methyl)-1h-pyrazol-5-yl)-2-fluoro-3-(trifluoromethyl)benzamide
Reaction equation
Cl.[C:2]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)[N:7]=1)([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[F:25][C:26]1[C:34]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>C(Cl)Cl>[C:2]([C:6]1[CH:10]=[C:9]([NH:11][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][CH:33]=[C:34]([C:35]([F:36])([F:37])[F:38])[C:26]=2[F:25])[N:8]([CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)[N:7]=1)([CH3:5])([CH3:3])[CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To the mixture of Example 6B (293 mg, 1.129 mmol) and triethylamine (0.472 mL, 3.39 mmol) in CH2Cl2 (5 mL) cooled with an ice-bath was added 2-fluoro-3-(trifluoromethyl)benzoyl chloride (307 mg, 1.355 mmol) in one portion. The mixture was stirred at ambient temperature for 2 h, the solvent removed under reduced pressure and the residue purified by flash chromatography (silica gel, 10-60% EtOAc/hexane) to yield 420 mg (90%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24 (s, 9H), 1.58-1.97 (m, 4H), 3.55-3.78 (m, 2H), 4.06-4.20 (m, 3H), 6.30 (s, 1H), 7.57 (t, J=7.80 Hz, 1H), 8.01 (q, J=8.02 Hz, 2H), 10.42 (s, 1H); MS (ESI) m/z 414 (M+H)+, 412 (M−H)−.
Workup
- customthe solvent removed under reduced pressure
- customthe residue purified by flash chromatography (silica gel, 10-60% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-9ba6e2ff65914e72a92b1829337ac7ab
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173687B2
Reaction notes
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