Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(2,3,4,5-Tetrahydro-1h-pyrido[4,3-b]indol-7-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1h)-one dihydrochloride
Reaction equation
FC(F)(F)C(O)=O.S([N:18]1[C:26]2[CH:25]=[C:24]([N:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][N:34]=4)=[CH:29][C:28]3=[O:43])[CH:23]=[CH:22][C:21]=2[C:20]2[CH2:44][NH:45][CH2:46][CH2:47][C:19]1=2)(C1C=CC(C)=CC=1)(=O)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:60].Cl>>[ClH:60].[ClH:60].[CH2:44]1[C:20]2[C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH:32]=[CH:31][C:30]([C:33]5[CH:38]=[CH:37][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:35][N:34]=5)=[CH:29][C:28]4=[O:43])=[CH:25][C:26]=3[NH:18][C:19]=2[CH2:47][CH2:46][NH:45]1Participants
3
Reactant 2
Product 1
Procedure
1-(5-Tosyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)-4-(5-(trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one trifluoroacetic acid salt (163 mg, 0.248 mmol) was deprotected and converted to the dihydrochloride salt according to the procedure of Example 106 (step b) to provide the title compound (30 mg, 25%) as an orange solid: mp 308-313° C.; 1H NMR (500 MHz, CD3OD) δ 9.04 (s, 1H), 8.28 (dd, J=8.3, 2.2 Hz, 1H), 8.22 (d, J=8.2 Hz, 1H), 7.81 (d, J=7.0 Hz, 1H), 7.62 (d, J=8.3 Hz, 1H), 7.46 (d, J=1.8 Hz, 1H), 7.38 (d, J=1.8 Hz, 1H), 7.24 (dd, J=7.1, 2.0 Hz, 1H), 7.11 (dd, J=8.3, 2.0 Hz, 1H), 4.49 (s, 2H), 3.65 (t, J=6.2 Hz, 2H), 3.21 (t, J=6.2 Hz, 2H); ESI MS m/z 411 [M+H]+; HPLC (Method B) 97.6% (AUC), tR=12.4 min.
Sources & evidence
- ORD record
- ord-00fb210e840a4e57881cb1bca741942d
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716308B2
Reaction notes
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