3-(4-Aminophenyl)-1,4-dimethylpiperazin-2-one → 1,4-Dimethyl-3-(4-{7-[3-(morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one

HRID 1262239Notes

Reaction equation

HRID 1262239 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:32]=[CH:31][C:30]([CH:33]2[N:38]([CH3:39])[CH2:37][CH2:36][N:35]([CH3:40])[C:34]2=[O:41])=[CH:29][CH:28]=1>>[CH3:40][N:35]1[CH2:36][CH2:37][N:38]([CH3:39])[CH:33]([C:30]2[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:9])=[O:8])[CH:11]=5)[N:24]4[N:23]=3)=[CH:28][CH:29]=2)[C:34]1=[O:41]

Participants

3

Reactant 2

HCID 576251203-(4-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 1785273257-[3-(Morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 667113441,4-Dimethyl-3-(4-{7-[3-(morpholine-4-sulfonyl)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino}-phenyl)-piperazin-2-one

Procedure

1,4-Dimethyl-3-(4-{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-(4-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1052a. Product isolated as an orange foam (91 mg, 55%). LCMS (m/e) 562 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.75 (s, 1H), 8.57 (d, 1H, J=7.5 Hz), 8.30 (s, 1H), 7.78-7.65 (m, 2H), 7.58 (d, 2H, J=8.3 Hz), 7.38 (d, 2H, J=8.3 Hz), 7.05 (d, 1H, J=4.7 Hz), 6.90 (bs, 1H), 6.86 (d, 1H, J=4.7 Hz), 3.80-3.68 (m, 6H), 3.27-3.19 (m, 1H), 3.12-3.00 (m, 5H), 3.00 (s, 3H), 2.74-2.63 (m, 1H), 2.21 (s, 3H).

Sources & evidence

ORD record
ord-947a300dca694ca6a2b729abb6a6bd49
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…