3-(3-Aminophenyl)-1,4-dimethylpiperazin-2-one → HCID 66712051, compound

HRID 1262248Notes

Reaction equation

HRID 1262248 reaction equation
O[C:2]1[N:7]=[CH:6][C:5]2=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:4]2[N:3]=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:30]2[N:35]([CH3:36])[CH2:34][CH2:33][N:32]([CH3:37])[C:31]2=[O:38])[CH:27]=[CH:28][CH:29]=1>>[CH3:36][N:35]1[CH2:34][CH2:33][N:32]([CH3:37])[C:31](=[O:38])[CH:30]1[C:26]1[CH:25]=[C:24]([NH:23][C:2]2[N:7]=[CH:6][C:5]3=[CH:8][CH:9]=[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])[N:4]3[N:3]=2)[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 574160813-(3-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 178482109HCID 178482109, compound

Product 1

HCID 66712051HCID 66712051, compound

Procedure

N-(2-{2-[3-(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 N-[2-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide and 3-(3-amino-phenyl)-1,4-dimethyl-piperazin-2-one in an analogous manner to Example 1052a. Product isolated as a brown foam (72 mg, 46%). LCMS (m/e) 520 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.72 (s, 1H), 7.89-7.82 (m, 1H), 7.54-7.45 (m, 4H), 7.38 (s, 1H), 7.20-7.12 (m, 1H), 7.02-6.92 (m, 2H), 6.89-6.81 (m, 2H), 3.70-3.60 (m, 1H), 3.52 (s, 1H), 3.24-3.15 (m, 1H), 3.11 (s, 3H), 3.01-2.92 (m, 1H), 2.97 (s, 3H), 2.68-2.55 (m, 1H), 2.62 (s, 3H), 2.08 (s, 3H).

Sources & evidence

ORD record
ord-8300959193a04a87be74dad4a0273fea
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…