(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → (R)-N-(2,2,2-Trifluoroethyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[F:21][C:22]([F:38])([F:37])[CH2:23][NH:24][C:25](=O)[O:26]C1C=CC([N+]([O-])=O)=CC=1>CC#N>[F:21][C:22]([F:38])([F:37])[CH2:23][NH:24][C:25]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)=[O:26]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (150 mg, 541 μmol, Example 87, Step 3) in MeCN (2 mL) was added 4-nitrophenyl 2,2,2-trifluoroethylcarbamate (286 mg, 1082 μmol). The resulting mixture was then subjected to a microwave irradiation at 100° C. for 15 min. Then, the solvent was removed and the residue was dissolved in a solution of DMSO and MeOH (1:1, 2 mL). The solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired product, which was then dissolved in MeOH (2.0 mL). The solution was then washed through PL-HCO3 MP-resin and the resin was then washed with MeOH (2×2 mL). The combined washings were concentrated and dried under vacuum to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 403 (M+H).
Workup
- customThe resulting mixture was then subjected to a microwave irradiation at 100° C. for 15 min
- customThen, the solvent was removed
- dissolutionthe residue was dissolved in a solution of DMSO and MeOH (1:1, 2 mL)
- customThe solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)
Sources & evidence
- ORD record
- ord-79265e6dad5c4b328c3387bed0a44fa7
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476297B2
Reaction notes
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