Reaction equation
[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:15][CH:16]([C:23]1(CN)[CH2:27][CH2:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:30][N:31](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCN(C(C)C)C(C)C>[Cl:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:15][CH:16]([C:23]1([NH:31][CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-chloro-3-(trifluoromethyl)benzoic acid (0.728 g; 3.24 mmol) in DMF (20 ml) and DIPEA (2.5 ml) was added (±)-{[amino(phenyl)methyl]cyclopentyl}methylamine D29 (1.0 g; 3.60 mmol) and HATU (1.23 g; 3.24 mmol). The resulting mixture was allowed to stir at room temperature overnight and then DMF evaporated off in vacuo. Residual material was partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4) and the filtrate evaporated in vacuo. The desired product was isolated by column chromatography on silica gel using 20% diethyl ether to 100% diethyl ether in n-pentane to afford the title compound as a white solid (0.908 g; 61%). 1H NMR (CDCl3) δ: 1.47-1.83 (9H, m), 2.21 (3H, s), 5.1 (1H, m), 7.23-7.43 (6H, m), 7.58 (1H, m), 7.65 (1H, m), 7.73 (1H, m); Mass Spectrum (Electrospray LC/MS), API+: Found 411 (MH+). C21H2235ClF3N2O requires 410. Ret. time 2.04 min.
Workup
- customDMF evaporated off in vacuo
- customResidual material was partitioned between ethyl acetate and water
- dry with materialThe organic layer was dried (Na2SO4)
- customthe filtrate evaporated in vacuo
Sources & evidence
- ORD record
- ord-52e008b438bc49e8b5555b7bdf07b14c
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745642B2
Linked notes
Loading…