Sodium Bicarbonate → N-(cyclopropylmethyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3 yl)phenyl)ethanamine
Reaction equation
[CH:1]1([CH2:4][N:5]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=4)[N:22]=3)=[CH:17][CH:16]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>>[CH:1]1([CH2:4][NH:5][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]=[CH:24][N:23]([C:26]4[CH:27]=[CH:28][C:29]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:30][CH:31]=4)[N:22]=3)=[CH:19][CH:20]=2)[CH2:3][CH2:2]1Participants
3
Procedure
The title compound was prepared from tert-butyl (cyclopropylmethyl)(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate (CB66), neutralized with aqueous sodium bicarbonate, and isolated as a white solid (0.125 g, 100%): mp 162-166° C.; 1H NMR (400 MHz, CDCl3) δ 8.54 (s, 1H), 8.15-8.09 (m, 2H), 7.81-7.75 (m, 2H), 7.38 (dq, J=8.9, 0.9 Hz, 2H), 7.34-7.29 (m, 2H), 3.22 (dd, J=10.2, 6.0 Hz, 2H), 3.09 (dd, J=10.0, 6.1 Hz, 2H), 2.84 (d, J=7.3 Hz, 2H), 1.11 (ddd, J=12.7, 8.1, 4.8 Hz, 1H), 0.86 (dd, J=12.8, 5.8 Hz, 1H), 0.69-0.58 (m, 2H), 0.37-0.29 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 403 ([M+H]+).
Sources & evidence
- ORD record
- ord-9bc75bf2ea054445955bd8ef5fc7168b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029560B2
Reaction notes
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