Hydrogen Bromide → 1-Methyl-1-N-[5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine
Reaction equation
[CH3:1][C:2]1([NH:21][C:22]2[CH: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[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH2:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl N-(2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl)carbamate in acetic acid (3 ml) was added HBr (6 M, 1.68 ml, 10.10 mmol). The reaction was sealed and heated at 90° C. for 24 hours. To this was then added further HBr (6 M, 1.68 ml, 10.10 mmol) and the reaction was heated at 90° C. for 24 hours. The reaction was concentrated in vacuo and the resulting residue was purified by SCX chromatography (2M ammonia in methanol). The product was purified by reverse phase chromatography (C18 silica, 5-100% water (with 0.05% ammonia)/acetonitrile) to afford the title compound as a single trans-enantiomer.
Workup
- customThe reaction was sealed
- temperaturethe reaction was heated at 90° C. for 24 hours
- concentrationThe reaction was concentrated in vacuo
- customthe resulting residue was purified by SCX chromatography (2M ammonia in methanol)
- customThe product was purified by reverse phase chromatography (C18 silica, 5-100% water (with 0.05% ammonia)/acetonitrile)
Sources & evidence
- ORD record
- ord-120ef5834a5248e9ad55bca9e94a8166
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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