[CH3:1][C:2]1([NH:21][C:22]2[N:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7]C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)C.Br>C(O)(=O)C>[CH3:1][C:2]1([NH:21][C:22]2[N:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][N:27]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH2:7]To a solution of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl N-(2-methyl-2-{[5-(trifluoromethyl)pyrimidin-2-yl]amino}cyclopentyl)carbamate (1.04 g, 2.35 mmol) in acetic acid (8 ml) was added HBr (1.28 ml, 23.48 mmol). The reaction was heated sealed and heated at 90° C. overnight. To this was then added further HBr (1.28 ml, 23.48 mmol) and the reaction mixture heated at 90° C. for 24 hours. Further acetic acid (5 ml) and HBr (5 ml) was added and the reaction mixture heated to 90° C. for 5 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene. The resulting residue was purified by SCX chromatography (2M ammonia in methanol) to afford the title compound as a single trans-enantiomer.
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