Water → 3-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinone

HRID 1295697Notes

Reaction equation

HRID 1295697 reaction equation
Cl[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[OH-:21].[Na+].O>CS(C)=O>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2](=[O:21])[NH:3][CH:4]=[CH:5][N:6]=2)[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 590138923-(4-tert-Butoxycarbonyl-1-piperazinyl)-2(1H)-pyrazinoneYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Chloro-3-(4-tert-butoxycarbonyl-1-piperazinyl)pyrazine* (60 g, 0.20 mol) was added to a mixture of NaOH (100 g, 2.50 mol), water (100 mL) and DMSO (100 g) at 100° C. After being stirred for 3 h, the mixture was allowed to cool and partitioned between toluene (100 g) and water (200 mL). Water (300 mL), crushed ice (200 g), EtOAc (600 g) and sodium chloride (100 g) were added to the aqueous layer. The layers were separated and the aqueous layer was extracted with an additional portion of EtOAc (600 g). The combined organic layers were concentrated in vacuo to furnish 38 g (68%) of the title product. 1H and 13C NMR data support the stated structure. HPLC purity: 100%. HRMS m/z calcd for C13H20N4O3 (M)+ 280.1535, found 280.1530. *Prepared according to the procedure described in WO 00/76984, Example 52, Step 1.

Workup

  1. temperatureto cool
  2. custompartitioned between toluene (100 g) and water (200 mL)
  3. customWater (300 mL), crushed ice (200 g), EtOAc (600 g) and sodium chloride (100 g)
  4. additionwere added to the aqueous layer
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with an additional portion of EtOAc (600 g)
  7. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-69c2d0ad0b724a0b9ae60d5f423dfb67
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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