1-Chloro-2-methanesulfonylethane → [3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-[8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-amine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[C:14]2[N:15]([N:19]=[C:20]([NH:22][C:23]3[CH:33]=[CH:32][C:26]4[CH2:27][CH2:28][NH:29][CH2:30][CH2:31][C:25]=4[CH:24]=3)[N:21]=2)[CH:16]=[CH:17][CH:18]=1.Cl[CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38]>>[CH3:40][S:37]([CH2:36][CH2:35][N:29]1[CH2:28][CH2:27][C:26]2[CH:32]=[CH:33][C:23]([NH:22][C:20]3[N:21]=[C:14]4[C:13]([C:4]5[CH:5]=[C:6]([C:9]([F:11])([F:10])[F:12])[CH:7]=[CH:8][C:3]=5[O:2][CH3:1])=[CH:18][CH:17]=[CH:16][N:15]4[N:19]=3)=[CH:24][C:25]=2[CH2:31][CH2:30]1)(=[O:39])=[O:38]Participants
3
Reactant 2
Product 1
Procedure
[3-(2-Methanesulfonyl-ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-[8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-amine was prepared from [8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.200 g, 0.441 mmol) and 1-chloro-2-methanesulfonyl-ethane (0.126 g, 0.882 mmol) in a manner analogous to Example 320b to give product (0.150 g, 61%). MP=194-196° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.80 (d, 1H), 7.95 (s, 1H), 7.82 (d, 1H), 7.62 (d, 1H), 7.40 (m, 3H), 7.08 (t, 1H), 7.00 (d, 1H), 3.85 (s, 3H), 3.28 (m, 2H), 3.05 (s, 3H), 2.85 (m, 2H), 2.75 (m, 4H), 2.60 (m, 4H): MS=560 (MH)+.
Sources & evidence
- ORD record
- ord-34e2ac980eb540e8a3296979384dd7f6
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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