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

HRID 2272999Notes

Reaction equation

HRID 2272999 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:7].Cl[C:9]1[C:10]2[N:11]([N:15]=[C:16]([NH2:18])[N:17]=2)[CH:12]=[CH:13][N:14]=1.Cl[C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=1>CN(C=O)C>[CH3:27][O:26][C:24]1[CH:25]=[C:20]([NH:18][C:16]2[N:17]=[C:10]3[C:9]([N:4]4[CH2:5][CH2:6][NH:1][C:2](=[O:7])[CH2:3]4)=[N:14][CH:13]=[CH:12][N:11]3[N:15]=2)[CH:21]=[C:22]([O:28][CH3:29])[CH:23]=1

Participants

5

Reactant 3

HCID 815021-Chloro-3,5-dimethoxybenzeneHCID 231360Piperazin-2-oneHCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

Product 1

HCID 717217704-[2-(3,5-Dimethoxy-phenylamino)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

Piperazin-2-one (1.1 eq), 8-chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine (1 eq) are dissolved in DMF and heated to 180° C. in a microwave for 1 h following general procedure 3. The intermediate is reacted with 1-chloro-3,5-dimethoxy-benzene under amination conditions as described in general procedure 3 giving the title compound as a solid.

Sources & evidence

ORD record
ord-c752705dd04d427f8705a72f5dd870ca
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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