Methylamine → 2-{[5-(Trifluoromethyl)pyridin-2-yl]methyl}cyclopentan-1-amine
Reaction equation
CN.[F:3][C:4]([F:29])([F:28])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[N:9][CH:10]=1>C(O)C>[F:28][C:4]([F:3])([F:29])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[NH2:17])=[N:9][CH:10]=1Participants
Procedure
Methanamine (40% aq, 3 ml, 34.7 mmol) was added to a solution of 2-(2-{[5-(trifluoromethyl)pyridin-2-yl]methyl}cyclopentyl)-2,3-dihydro-1H-isoindole-1,3-dione (0.316 g, 0.84 mmol) in ethanol (5 ml). The reaction was stirred at room temperature for 24 hours and then further methanamine (40% aq, 3 ml, 34.7 mmol) was added. The reaction was stirred for 24 hours at room temperature and then re-suspended in ethanol (5 ml) and methanamine (40% aq, 3 ml, 34.7 mmol). The reaction stirred for 72 hours at room temperature. The reaction mixture was concentrated in vacuo and was then purified by reverse phase preparative HPLC (eluted with acetonitrile/water with 0.1% ammonia) and then purified by column chromatography (basic silica, 50-100% ethyl acetate/petrol) to afford the title compound.
Workup
- stirringThe reaction was stirred for 24 hours at room temperature
- stirringThe reaction stirred for 72 hours at room temperature
- concentrationThe reaction mixture was concentrated in vacuo
- customwas then purified by reverse phase preparative HPLC (eluted with acetonitrile/water with 0.1% ammonia)
- custompurified by column chromatography (basic silica, 50-100% ethyl acetate/petrol)
Sources & evidence
- ORD record
- ord-1fc81679fe5b409ab91e23b43e22b397
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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