1-Methylpiperazine → HCID 178461881, compound

HRID 1051785Notes

Reaction equation

HRID 1051785 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][NH:20]3)[CH3:14])[N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>O1CCOCC1>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([N:29]1[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]1)=[N:3][C:4]([C@@H:13]([NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]3[C:17]=1[N:18]=[CH:19][NH:20]3)[CH3:14])=[CH:5]2

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 178461880HCID 178461880, compound

Product 1

HCID 178461881HCID 178461881, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of (S)—N-(1-(1,8-dichloroisoquinolin-3-yl)ethyl)-9H-purin-6-amine 38 (300 mg, 0.84 mmol, 1 eq) in 1,4-dioxane (10 mL) at RT, 1-methylpiperazine (167 mg, 1.68 mmol, 2 eq) was added and the resulting mixture was stirred at reflux for 8 h. The mixture was allowed to cool to RT, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM) to afford the product, (S)—N-(1-(8-chloro-1-(4-methylpiperazin-1-yl)isoquinolin-3-yl)ethyl)-9H-purin-6-amine 46. ESI-MS m/z: 423.2 [M+H]+.

Workup

  1. temperatureat reflux for 8 h
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM)

Sources & evidence

ORD record
ord-58b8a612f42c4a05bb107493ded4bc40
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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