3-(4-Aminophenyl)-1,4-dimethylpiperazin-2-one → N-(2-{2-[4-(1,4-Dimethyl-3-oxo-piperazin-2-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-N-methyl-methanesulfonamide

HRID 1262237Notes

Reaction equation

HRID 1262237 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].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]2[N:42]([CH3:43])[CH2:41][CH2:40][N:39]([CH3:44])[C:38]2=[O:45])=[CH:33][CH:32]=1>>[CH3:43][N:42]1[CH2:41][CH2:40][N:39]([CH3:44])[C:38](=[O:45])[CH:37]1[C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:18]2[N:17]=[CH:16][C:15]3=[CH:14][CH:13]=[C:12]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=4[N:5]([CH3:29])[S:2]([CH3:1])(=[O:4])=[O:3])[N:20]3[N:19]=2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 576251203-(4-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 86661681Trifluoro-methanesulfonic acid 7-[2-(methanesulfonyl-methyl-amino)-phenyl]-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

Product 1

HCID 66711921N-(2-{2-[4-(1,4-Dimethyl-3-oxo-piperazin-2-yl)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-7-yl}-phenyl)-N-methyl-methanesulfonamide

Procedure

N-(2-{2-[4-(1,4-Dimethyl-3-oxo-piperazin-2-yl)-phenylamino]-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 3-(4-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1061. Product isolated as an orange foam (80 mg, 53%). LCMS (m/e) 520 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 7.95-7.88 (m, 1H), 7.58-7.46 (m, 3H), 7.45 (d, 2H, J=8.4 Hz), 7.20 (d, 2H, J=8.4 Hz), 7.03 (d, 1H, J=4.7 Hz), 6.87 (d, 1H, J=4.7 Hz), 6.82 (bs, 1H), 3.77-3.67 (m, 1H), 3.64 (s, 1H), 3.24-3.17 (m, 1H), 3.11 (s, 3H), 3.05-2.96 (m, 1H), 2.98 (s, 3H), 2.70 (s, 3H), 2.69-2.61 (m, 1H), 2.16 (s, 3H).

Sources & evidence

ORD record
ord-f1e84a7a992d4a2fa53f68a3da106b8b
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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