1-(Methylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-amine → N-{2-[2-(1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide
Reaction equation
[CH3:1][S:2]([N:5]([CH3:29])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:20]2[C:15]([CH:16]=[N:17][C:18](OS(C(F)(F)F)(=O)=O)=[N:19]2)=[CH:14][CH:13]=1)(=[O:4])=[O:3].[CH3:30][S:31]([N:34]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([NH2:44])[CH:42]=2)[CH2:37][CH2:36][CH2:35]1)(=[O:33])=[O:32]>>[CH3:30][S:31]([N:34]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([NH:44][C:18]3[N:17]=[CH:16][C:15]4=[CH:14][CH:13]=[C:12]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]([CH3:29])[S:2]([CH3:1])(=[O:3])=[O:4])[N:20]4[N:19]=3)[CH:42]=2)[CH2:37][CH2:36][CH2:35]1)(=[O:33])=[O:32]Participants
Reactant 2
Product 1
Procedure
N-{2-[2-(1-Methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-N-methyl-methanesulfonamide was prepared from Trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester and 1-methanesulfonyl-1,2,3,4-tetrahydro-quinolin-7-ylamine in an analogous manner to Example 1061. Product isolated as a yellow foam (61 mg, 55%). LCMS (m/e) 527 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.73 (s, 1H), 7.94-7.87 (m, 1H), 7.68-7.62 (m, 1H), 7.56-7.44 (m, 3H), 7.40 (dd, 1H, J=1.7 and 8.3 Hz), 7.00 (d, 1H, J=4.7 Hz), 6.96 (d, 1H, J=8.3 Hz), 6.87 (d, 1H, J=4.7 Hz), 6.79 (bs, 1H), 3.82-3.73 (m, 2H), 3.13 (s, 3H), 2.82-2.74 (m, 2H), 2.78 (s, 3H), 2.64 (s, 3H), 2.01-1.92 (m, 2H).
Sources & evidence
- ORD record
- ord-9ca30c96c6404850983c18ec04da8629
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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