trans-3-Amino-4-methoxypyrrolidine dihydrochloride → 6-(trans-3-Amino-4-methoxypyrrolidin-1-yl)-5-(1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide
Reaction equation
Cl[C:2]1[C:21]([C:22]2[NH:26][N:25]=[CH:24][CH:23]=2)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.Cl.Cl.[CH3:29][O:30][C@@H:31]1[CH2:35][NH:34][CH2:33][C@H:32]1[NH2:36]>>[NH2:36][C@H:32]1[C@H:31]([O:30][CH3:29])[CH2:35][N:34]([C:2]2[C:21]([C:22]3[NH:26][N:25]=[CH:24][CH:23]=3)=[CH:20][C:5]([C:6]([NH:8][C:9]3[CH:10]=[CH:11][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=3)=[O:7])=[CH:4][N:3]=2)[CH2:33]1Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 38 using 6-chloro-5-(1H-pyrazol-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 38.1) and trans-4-methoxypyrrolidin-3-amine dihydrochloride (Stage 78.1) to afford a white solid. HPLC (Condition 7) tR=5.675 min, UPLC-MS (Condition 3) tR=0.78 min, m/z=463.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.58 (br. s, 2H) 2.83-2.98 (m, 1H) 3.07-3.18 (m, 1H) 3.21 (s, 3H) 3.26-3.43 (m, 2H) 3.45-3.59 (m, 2H) 6.39 (br. s, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.49-7.91 (m, J=8.60 Hz, 3H) 8.03 (br. s, 1H) 8.72 (br. s, 1H) 10.18 (s, 1H) 12.76-13.24 (m, 1H).
Workup
- customto afford a white solid
Sources & evidence
- ORD record
- ord-ff226d1bf2a544f399ebd88494d27887
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340537B2
Reaction notes
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