Sodium hydride → 2-(2H-1,2,3-Triazol-2-yl)-N-[(1S,2S)-2-{[4-(trifluoromethyl)pyridin-2-yl]oxy}cyclopentyl]benzamide
Reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[N:19]=[CH:18][CH:17]=[N:16]1.[H-].[Na+].Cl[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=1>CN(C=O)C>[N:19]1[N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([NH:7][C@H:3]2[CH2:4][CH2:5][CH2:6][C@@H:2]2[O:1][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=2)=[O:20])[N:16]=[CH:17][CH:18]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-[(1S,2S)-2-hydroxycyclopentyl]-2-(2H-1,2,3-triazol-2-yl)benzamide (Intermediate 11; 200 mg, 0.73 mmol) in dry DMF (1.2 ml) was added sodium hydride (60% dispersion in mineral oil, 29.4 mg, 0.73 mmol). To this was then added 2-chloro-4-(trifluoromethyl)pyridine (CAS number 81565-18-6; 133 mg, 0.73 mmol) as a solution in dry DMF (1.2 ml). The reaction was stirred at room temperature for 17 hours and was then partitioned between ethyl acetate and water. The organics were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The crude oil was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.
Workup
- customwas then partitioned between ethyl acetate and water
- washThe organics were washed with water and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe crude oil was purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)
Sources & evidence
- ORD record
- ord-b00d56a7316641cc85e21ddc06d31015
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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