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]1([F:41])[CH2:27][CH2:26][CH:25]([NH:28][C:29](=O)[O:30]C2C=CC([N+]([O-])=O)=CC=2)[CH2:24][CH2:23]1.CO>CC#N>[F:21][C:22]1([F:41])[CH2:23][CH2:24][CH:25]([NH:28][C:29]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:30])[CH2:26][CH2:27]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (80 mg, 0.29 mmol) in MeCN (2 mL) was added 4-nitrophenyl 4,4-difluoro-cyclohexylcarbamate (217 mg, 0.72 mmol). The resulting mixture was then subjected to microwave irradiation at 120° C. for 15 min. Then, MeOH (0.5 mL) was added and the mixture was filtered. The filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the title compound, which was dissolved in MeOH (1 mL). The solution was then passed through PL-HCO3 and the resin was washed with MeOH (2×0.3 mL). The combined filtrates were concentrated and dried in vacuo to give the title compound as a light-yellow solid. MS (ESI, positive ion) m/z: 439 (M+H).
Workup
- customirradiation at 120° C. for 15 min
- filtrationthe mixture was filtered
- customThe filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)
Sources & evidence
- ORD record
- ord-f8b4985b3b3749aabaadeb4cf7bc08a5
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476297B2
Linked notes
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