Water → HCID 22036287, compound

HRID 1789754Notes

Reaction equation

HRID 1789754 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Br:20]Br.O>CC(O)=O>[Br:20][C:4]1[N:3]=[C:2]([Cl:1])[C:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24408BromineHCID 140864382-Chloro-3-(piperazin-1-yl)pyrazine

Product 1

HCID 22036287HCID 22036287, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 2-chloro-3-(1-piperazinyl)pyrazine (5.94 g, 30 mmol, from Example 90, Step 1) and Na2CO3 (6.0 g, 57 mmol) in AcOH (25 mL) was added a solution of Br2 (6.00 g 38.0 mmol) in AcOH (25 mL) dropwise at room temperature. The reaction mixture was stirred overnight. Water (50 mL) was added and the solution was stirred for 30 min and then concentrated to a small volume. Water (20 mL) was added and the solution was basified to pH 9 by adding solid Na2CO3. The mixture was extracted with CH2Cl2 containing 10% MeOH. The combined extract was evaporated to dryness and the residue was recrystallized from MeOH to give 7.43 g (89%) of the title compound: mp 114-115° C. HRMS m/z calcd for C8H10BrCIN4 (M)+275.9777, found 275.9765.

Workup

  1. stirringthe solution was stirred for 30 min
  2. concentrationconcentrated to a small volume
  3. additionWater (20 mL) was added
  4. additionby adding solid Na2CO3
  5. extractionThe mixture was extracted with CH2Cl2 containing 10% MeOH
  6. extractionThe combined extract
  7. customwas evaporated to dryness
  8. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-310dc38479534f7198d45f099cab02c6
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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