1-Chloro-3,5-dimethoxybenzene → (3,5-Dimethoxy-phenyl)-[8-(4-methyl-2-phenyl-piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-amine

HRID 2273004Notes

Reaction equation

HRID 2273004 reaction equation
Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][N:7]=1.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14]1.Cl[C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=1>>[CH3:33][O:32][C:30]1[CH:31]=[C:26]([NH:11][C:9]2[N:10]=[C:3]3[C:2]([N:16]4[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH:15]4[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[N:7][CH:6]=[CH:5][N:4]3[N:8]=2)[CH:27]=[C:28]([O:34][CH3:35])[CH:29]=1

Participants

4

Reactant 3

HCID 815021-Chloro-3,5-dimethoxybenzeneHCID 27600091-Methyl-3-phenylpiperazineHCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

Product 1

HCID 89767138(3,5-Dimethoxy-phenyl)-[8-(4-methyl-2-phenyl-piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]-amine

Procedure

8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine and 1-methyl-3-phenyl-piperazine are coupled according general procedure 3. The intermediate is isolated and Buchwald Hartwig Amination following general procedure 2 with 1-chloro-3,5-dimethoxy-benzene gives the title compound as a solid.

Workup

  1. customThe intermediate is isolated

Sources & evidence

ORD record
ord-0aa383ca693b4201bfa2d4a6f9d7f054
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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