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

HRID 1262247Notes

Reaction equation

HRID 1262247 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](O)=[N:16]2)=[CH:11][CH:10]=1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:26]2[N:31]([CH3:32])[CH2:30][CH2:29][N:28]([CH3:33])[C:27]2=[O:34])[CH:23]=[CH:24][CH:25]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]4[N:31]([CH3:32])[CH2:30][CH2:29][N:28]([CH3:33])[C:27]4=[O:34])[CH:23]=[CH:24][CH:25]=3)=[N:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 574160813-(3-Aminophenyl)-1,4-dimethylpiperazin-2-oneHCID 1784892767-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

Product 1

HCID 667123763-{3-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-1,4-dimethyl-piperazin-2-one

Procedure

3-{3-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-1,4-dimethyl-piperazin-2-one was prepared from 7-(2-methoxy-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 brown foam (61 mg, 45%). LCMS (m/e) 443 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.69 (s, 1H), 7.97-7.89 (m, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.45-7.36 (m, 2H), 7.25-7.17 (m, 1H), 7.15-7.08 (m, 1H), 7.05 (d, 1H, J=8.3 Hz), 7.00 (d, 1H, J=4.6 Hz), 6.96 (d, 1H, J=7.6 Hz), 6.89 (s, 1H), 6.83 (d, 1H, J=4.6 Hz), 3.84 (s, 3H), 3.73-3.64 (m, 1H), 3.63 (s, 1H), 3.26-3.17 (m, 1H), 3.03-2.94 (m, 1H), 2.99 (s, 3H), 2.69-2.58 (m, 1H), 2.09 (s, 3H).

Sources & evidence

ORD record
ord-42de6158e3c746158639b9ae9c614011
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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