Water → HCID 67480855, compound

HRID 1295726Notes

Reaction equation

HRID 1295726 reaction equation
Cl[C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:10]([CH3:21])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.C[C:23]([O-:26])([CH3:25])C.[K+].[OH2:28]>C(O)CO.O1CCOCC1>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:3]2[C:2]([O:28][CH2:25][CH2:23][OH:26])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:9][CH:10]1[CH3:21])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86760515HCID 86760515, compound

Product 1

HCID 67480855HCID 67480855, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of tert-butyl 4-(3-chloropyrazin-2-yl)-2-methylpiperazine-1-carboxylate (3.0 g, 9.6 mmol; from Step 2) in ethylene glycol (10 mL) and dioxane (30 mL) was added t-BuOK (1.18 g, 10.6 mmol). The resulting mixture was stirred at 90° C., under N2, overnight. Water (10 mL) was added to the light brown reaction mixture and extracted with dichloromethane (3×20 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography using toluene/EtOAc (2:3) as eluent to furnish 3.19 g (98%) of the title compound. HPLC purity: 99%. MS m/z 339 (M+H)+. HRMS m/z calcd for C16H26N4O4(M)+ 338.1954, found 338.1953.

Workup

  1. extractionextracted with dichloromethane (3×20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9b047ae8a5294ab98eb48cc7eadcfbce
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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