methyl 3-(6-(cyclohexyl(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methylamino)nicotinamido)propanoate → 3-(6-(cyclohexyl(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methylamino)nicotinamido)propanoic acid
Reaction equation
[CH:1]1([N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[N:31]3)=[CH:26][C:25]=2[CH3:39])[C:8]2[CH:22]=[CH:21][C:11]([C:12]([NH:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[O:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)=O.CC(O)C>>[CH:1]1([N:7]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[N:31]3)=[CH:26][C:25]=2[CH3:39])[C:8]2[CH:22]=[CH:21][C:11]([C:12]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared by a method analogous to that described in Step D of Example 82, using Isomer 2 of methyl 3-(6-(cyclohexyl(2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenyl)methylamino)nicotinamido)propanoate. 1H NMR (400 MHz, CD3OD, δ): 8.68 (s, 1H), 8.41 (d, 1H), 7.95 (s, 1H), 7.72-7.75 (m, 1H), 7.54-7.57 (m, 2H), 7.45 (d, 1H), 6.49 (d, 1H), 5.08 (d, 1H), 3.55 (t, 2H), 2.56-2.60 (m, 5H), 2.08 (m, 1H), 1.68-1.79 (m, 4H), 1.40-1.50 (m, 1H), 1.00-1.35 (m, 5H). MS (M+1) 530.1. Chiral SFC: Chiralpak AD-3, 4.6×50 mm, 3 μm. Modifier: 0.05% DEA. Mobile Phase: 60/40 CO2/2-propanol. Flow: 4 mL/min. Retention time: 1.46 minutes, 100% ee (Isomer 2).
Sources & evidence
- ORD record
- ord-3d45942720ce4af48671cddb9ca16b1b
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859591B2
Reaction notes
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