4-(Pyridin-3-yl)aniline → N-Methyl-N-{2-[2-(4-pyridin-3-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide
Reaction equation
O[C:2]1[N:7]=[CH:6][C:5]2=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:4]2[N:3]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH:24]=1>>[CH3:22][N:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[N:4]2[C:5]([CH:6]=[N:7][C:2]([NH:35][C:32]3[CH:31]=[CH:30][C:29]([C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[CH:34][CH:33]=3)=[N:3]2)=[CH:8][CH:9]=1)[S:18]([CH3:21])(=[O:20])=[O:19]Participants
3
Procedure
N-Methyl-N-{2-[2-(4-pyridin-3-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-methanesulfonamide was prepared from N-[2-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide and 4-pyridin-3-yl-phenylamine in an analogous manner to Example 1052a. Product isolated as a yellow foam (71 mg, 50%). LCMS (m/e) 471 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.82 (s, 1H), 8.75 (s, 1H), 8.55 (d, 1H, J=4.6 Hz), 8.00-7.91 (m, 1H), 7.83 (d, 1H, J=8.1 Hz), 7.60 (d, 2H, J=7.9 Hz), 7.59-7.49 (m, 3H), 7.45 (d, 2H, J=7.7 Hz), 7.39-7.30 (m, 1H), 7.07 (d, 1H, J=4.0 Hz), 6.95-6.85 (m, 2H), 3.15 (s, 3H), 2.72 (s, 3H).
Sources & evidence
- ORD record
- ord-d222ff827e724e5facc042dbdb1f19e7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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