Ethylene Glycol → 2-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

HRID 493285Notes

Reaction equation

HRID 493285 reaction equation
O(C(C)(C)C)[K].Cl[C:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:12][CH:11]=[CH:10][N:9]=1.[CH2:27]([OH:30])[CH2:28][OH:29]>N1C=CC=CC=1>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:13]2[C:8]([O:29][CH2:28][CH2:27][OH:30])=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanolYield 85.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

KO-t-Bu (9.92 g, 103 mmol) was added to a mixture of the product obtained in Step 1 (18.14 g, 60.7 mmol) and ethylene glycol (25 mL, 448 mmol) in pyridine (125 mL) at 85° C. The reaction mixture was stirred for 15 h and then poured into ice-water and extracted with toluene. The organic phase was dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel using toluene/EtOAc (1:1) as eluent to give 16.9 g (85%) of the title product. HRMS m/z calcd for C15H24N4O4 (M)+324.1798, found 324.1784.

Workup

  1. extractionextracted with toluene
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a41eb2da21a24ed69a66f190b2f45f62
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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