4-(4-Bromophenyl)morpholine → [8-(3-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-morpholin-4-yl-phenyl)-amine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Br[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:22]4[CH:23]=[CH:24][C:25]([N:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)=[CH:26][CH:27]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]Participants
3
Procedure
The title compound was prepared from 8-(3-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (100.0 mg, 0.3468 mmol) and 4-(4-bromo-phenyl)-morpholine (101.0 mg, 0.4172 mmol) in a manner analogous to Step 2d and was isolated as a pale yellow solid (0.025 g, 16%). MP=202-204° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.68 (t, J=1.6, 1H), 8.46 (dd, J=6.9, 0.9 Hz, 1H), 8.39-8.35 (m, 1H), 8.01-7.98 (m, 1H), 7.73 (dd, J=7.7, 7.7 Hz, 1H), 7.67 (dd, J=7.5, 0.8 Hz, 1H), 7.56-7.50 (m, 2H), 7.01-6.94 (m, 3H), 6.72 (s, 1H), 3.90-3.86 (m, 4H), 3.14-3.10 (m, 7H). MS=450 (MH)+.
Sources & evidence
- ORD record
- ord-0463e19ee58c4ce8bf0981d6ca48aa3b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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