Water → HCID 22036287, compound

HRID 991683Notes

Reaction equation

HRID 991683 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 C8H10BrClN4 (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-18ca163b640b4863bf120b2ea4c3a712
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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