1-(Ethanesulfonyl)piperazine → 3-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-phenylpyrazine-2-carboxamide

HRID 1959347Notes

Reaction equation

HRID 1959347 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.[CH2:18]([S:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)(=[O:22])=[O:21])[CH3:19]>>[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])=[N:4][C:5]([N:26]2[CH2:25][CH2:24][N:23]([S:20]([CH2:18][CH3:19])(=[O:21])=[O:22])[CH2:28][CH2:27]2)=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 4152941-(Ethanesulfonyl)piperazineHCID 529371483-amino-6-bromo-N-phenylpyrazine-2-carboxamide

Product 1

HCID 461992473-amino-6-(4-(ethylsulfonyl)piperazin-1-yl)-N-phenylpyrazine-2-carboxamideYield 58%

Procedure

3-amino-6-bromo-N-phenyl-pyrazine-2-carboxamide (50 mg, 0.1706 mmol) was heated in neat 1-ethylsulfonylpiperazine (excess) at 190° C. for 115 mins in the microwave. The mixture was partitioned between water and EtOAc and the aqueous layer separated. The organic phase was dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (41.2 mg, 58% Yield).

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. customthe aqueous layer separated
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  6. customThe fractions were collected
  7. customfreeze-dried

Sources & evidence

ORD record
ord-4d8a717c6e9248db841714a94601c4e1
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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