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

HRID 1262249Notes

Reaction equation

HRID 1262249 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17](O)=[N:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:21][C:22]1[CH:23]=[C:24]([CH:28]2[N:33]([CH3:34])[CH2:32][CH2:31][N:30]([CH3:35])[C:29]2=[O:36])[CH:25]=[CH:26][CH:27]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:19]3[C:14]([CH:15]=[N:16][C:17]([NH:21][C:22]4[CH:23]=[C:24]([CH:28]5[N:33]([CH3:34])[CH2:32][CH2:31][N:30]([CH3:35])[C:29]5=[O:36])[CH:25]=[CH:26][CH:27]=4)=[N:18]3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 574160813-(3-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 178504663HCID 178504663, compound

Product 1

HCID 667118633-{3-[7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-1,4-dimethyl-piperazin-2-one

Procedure

3-{3-[7-(4-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-1,4-dimethyl-piperazin-2-one was prepared from 7-(4-methanesulfonyl-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 (75 mg, 50%). LCMS (m/e) 491 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.76 (s, 1H), 8.38 (d, 2H, J=8.4 Hz), 8.05 (d, 2H, J=8.4 Hz), 7.68 (s, 1H), 7.51 (d, 1H, J=8.2 Hz) 7.37-7.29 (m, 1H), 7.11 (d, 1H, J=7.6 Hz), 7.08 (d, 1H, J=4.8 Hz), 6.91 (s, 1H), 6.86 (d, 1H, J=4.8 Hz), 3.75-3.65 (m, 1H), 3.66 (s, 1H), 3.25-3.18 (m, 1H), 3.10 (s, 3H), 3.08-3.00 (m, 1H), 2.99 (s, 3H), 2.77-2.67 (m, 1H), 2.18 (s, 3H).

Sources & evidence

ORD record
ord-ba775418214f4caf9b70652ff562eba1
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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