1-Methylpiperazine → HCID 118364848, compound

HRID 1478575Notes

Reaction equation

HRID 1478575 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:16][CH2:15][O:14][C@H:13]([CH2:17][N:18]3[C:22]4=[N:23][C:24]([C:27]5[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=5)=[CH:25][N:26]=[C:21]4[N:20]=[N:19]3)[CH2:12]2)=[N:9][CH:10]=1.[CH3:33][N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1>CN(C=O)C>[CH3:32][N:30]1[CH:31]=[C:27]([C:24]2[N:23]=[C:22]3[N:18]([CH2:17][C@H:13]4[O:14][CH2:15][CH2:16][N:11]([C:8]5[N:7]=[CH:6][C:5]([O:4][CH2:3][CH2:2][N:37]6[CH2:38][CH2:39][N:34]([CH3:33])[CH2:35][CH2:36]6)=[CH:10][N:9]=5)[CH2:12]4)[N:19]=[N:20][C:21]3=[N:26][CH:25]=2)[CH:28]=[N:29]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 118364845HCID 118364845, compound

Product 1

HCID 118364848HCID 118364848, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

(S)-4-(5-(2-chloroethoxy)pyrimidin-2-yl)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholine 9 mg (0.019 mmol) was dissolved in DMF 1 ml, and 1-methylpiperazine 4 μl (0.39 mmol) and KI 4 mg (0.022 mmol) were added. The mixture was stirred at 75° C. overnight. When the reaction was completed, the reaction mixture was extracted several times with ethyl acetate and brine, and the organic layer was dried over Na2SO4. Prep LC with 7% MeOH/MC gave a product 7.8 mg (76%).

Workup

  1. extractionthe reaction mixture was extracted several times with ethyl acetate and brine
  2. dry with materialthe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-0ea1c19cf01d4941a5f9a5ab66c5d49e
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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