3-Chloro-4-(trifluoromethyl)benzylamine → 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid 4-chloro-3-trifluoromethyl-benzylamide
Reaction equation
N[CH2:2][CH2:3][NH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]2[NH:19][CH:20]=[CH:21][C:14]=12)=[O:6].[Cl:22][C:23]1[CH:24]=[C:25](C=[CH:29][C:30]=1[C:31]([F:34])([F:33])[F:32])CN>>[Cl:22][C:23]1[CH:24]=[CH:25][C:2]([CH2:3][NH:4][C:5]([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[NH:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[NH:19][CH:20]=[CH:21][C:14]=23)=[O:6])=[CH:29][C:30]=1[C:31]([F:34])([F:33])[F:32]Participants
3
Procedure
This compound was prepared in an analogous manner as 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (2-amino-ethyl)-amide using 3-chloro-4-(trifluoromethyl)benzylamine instead of tert-butyl-2-amino ethyl carbamate. LCMS (ESI) 451 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (1H, br. s.) 10.24 (1H, s) 8.76 (1H, t, J=5.98 Hz) 8.02 (1H, d, J=5.47 Hz) 7.82 (2H, d, J=4.05 Hz) 7.65-7.71 (1H, m) 7.58-7.64 (1H, m) 7.50 (1H, d, J=5.42 Hz) 7.30 (1H, dd, J=3.29, 2.56 Hz) 6.84 (1H, d, J=5.42 Hz) 6.40 (1H, dd, J=3.49, 1.93 Hz) 4.52 (2H, d, J=5.91 Hz)
Sources & evidence
- ORD record
- ord-677154f03a9348cb9cf0b6664afcd5a4
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023847B2
Reaction notes
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