4-Bromo-1,2-dimethyl-1H-imidazole → [7-(1,2-Dimethyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine
Reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:8])[N:5]([CH3:7])[CH:6]=1.[N:9]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]3[N:27]=[CH:26][C:25]4=[CH:28][CH:29]=[C:30](B5OC(C)(C)C(C)(C)O5)[N:24]4[N:23]=3)=[CH:17][CH:16]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>>[CH3:7][N:5]1[CH:6]=[C:2]([C:30]2[N:24]3[C:25]([CH:26]=[N:27][C:22]([NH:21][C:18]4[CH:19]=[CH:20][C:15]([N:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)=[CH:16][CH:17]=4)=[N:23]3)=[CH:28][CH:29]=2)[N:3]=[C:4]1[CH3:8]Participants
3
Reactant 2
Product 1
Procedure
[7-(1,2-Dimethyl-1H-imidazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(4-morpholin-4-yl-phenyl)-amine was prepared from 4-bromo-1,2-dimethyl-1H-imidazole and (4-morpholin-4-yl-phenyl)-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine in an analogous manner to Example 1042b. Product isolated as a yellow solid (11 mg, 10%). m.p.=decomposed at 250° C.; LCMS (m/e) 390 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.62 (s, 1H), 7.85 (s, 1H), 7.55 (d, 2H, J=8.9 Hz), 7.27-7.23 (m, 1H), 6.97 (d, 2H, J=8.9 Hz), 6.81 (d, 1H, J=4.8 Hz), 6.56 (bs, 1H), 3.93-3.87 (m, 4H), 3.64 (s, 3H), 3.18-3.12 (m, 4H), 2.46 (s, 3H).
Sources & evidence
- ORD record
- ord-8056ed4919614a06b29adbd2d5724bf1
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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