3-(3-Aminophenyl)-1,4-dimethylpiperazin-2-one → 1,4-Dimethyl-3-(3-{7-[3-(morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one
Reaction equation
[N:1]1([S:7]([C:10]2[CH:11]=[C:12]([C:16]3[N:24]4[C:19]([CH:20]=[N:21][C:22](O)=[N:23]4)=[CH:18][CH:17]=3)[CH:13]=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:26][C:27]1[CH:28]=[C:29]([CH:33]2[N:38]([CH3:39])[CH2:37][CH2:36][N:35]([CH3:40])[C:34]2=[O:41])[CH:30]=[CH:31][CH:32]=1>>[CH3:40][N:35]1[CH2:36][CH2:37][N:38]([CH3:39])[CH:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([NH:26][C:22]3[N:21]=[CH:20][C:19]4=[CH:18][CH:17]=[C:16]([C:12]5[CH:13]=[CH:14][CH:15]=[C:10]([S:7]([N:1]6[CH2:2][CH2:3][O:4][CH2:5][CH2:6]6)(=[O:8])=[O:9])[CH:11]=5)[N:24]4[N:23]=3)[CH:28]=2)[C:34]1=[O:41]Participants
3
Procedure
1,4-Dimethyl-3-(3-{7-[3-(morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one was prepared from 7-[3-(morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol and 3-(3-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1052a. Product isolated as a yellow foam (84 mg, 49%). LCMS (m/e) 562 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.75 (s, 1H), 8.63 (d, 1H, J=7.5 Hz), 8.28 (s, 1H), 7.88-7.81 (m, 1H), 7.75-7.64 (m, 2H), 7.43-7.35 (m, 1H), 7.33 (s, 1H), 7.09 (d, 1H, J=7.6 Hz), 7.05 (d, 1H, J=4.8 Hz), 6.90 (s, 1H), 6.86 (d, 1H, J=4.8 Hz), 3.78-3.65 (m, 6H), 3.26-3.18 (m, 1H), 3.10-3.03 (m, 4H), 3.03-2.96 (m, 4H), 2.74-2.62 (m, 1H), 2.17 (s, 3H).
Sources & evidence
- ORD record
- ord-5094c4c4eda64691a584f8bd0cbef5a6
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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