HCID 10186648, compound → HCID 10160308, compound
Reaction equation
C([O:8][C:9]1[CH:37]=[CH:36][CH:35]=[CH:34][C:10]=1[O:11][C:12]1[CH:13]=[C:14]([N:18]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[S:19]([CH2:22][C:23]([F:26])([F:25])[F:24])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=1)C1C=CC=CC=1>CO.[Ni]>[OH:8][C:9]1[CH:37]=[CH:36][CH:35]=[CH:34][C:10]=1[O:11][C:12]1[CH:13]=[C:14]([N:18]([CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[S:19]([CH2:22][C:23]([F:25])([F:24])[F:26])(=[O:21])=[O:20])[CH:15]=[CH:16][CH:17]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N-(3-(2-benzyloxyphenoxy)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine (529 mg, 1.00 mmol) in methanol (50 mL) was carefully treated with Raney® nickel (one tsp.), placed on a Parr® apparatus, and hydrogenated at 45-50 psi pressure for 3 h. The mixture was carefully filtered through celite® under nitrogen without allowing the filter cake to dry, and the filtrate was concentrated in vacuo. The residual solid was triturated from petroleum ethers (30°-60°) to afford the title compound (394 mg, 90%) as a white solid; mp 57.5-60.0° C. The title compound was converted to the hydrochloride salt by treatment in methanol with ethereal HCl. 1H NMR: 8.50 (br s,1H), 8.25 (br s,1H), 7.68 (d,1H, J=8 Hz), 7.25-7.30 (m,2H); 6.95-7.10 (m,2H), 6.90-6.95 (m,2H), 6.70-6.85 (m,3H), 6.05 (br s,1H), 4.82 (s,2H), 3.75-3.85 (m,2H).MS calcd. 438.4; MS(M+1) 439.3
Workup
- filtrationThe mixture was carefully filtered through celite® under nitrogen
- customto dry
- concentrationthe filtrate was concentrated in vacuo
- customThe residual solid was triturated from petroleum ethers (30°-60°)
Sources & evidence
- ORD record
- ord-9d50956ba0ac44cca97e410de871a7cc
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06800651B2
Reaction notes
Loading…