HCID 58084376, compound → [3-Amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-phenyl-methanone

HRID 2174659Notes

Reaction equation

HRID 2174659 reaction equation
Br[Mg][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:9][C:10]1[C:11]([C:28](N(OC)C)=[O:29])=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:14][N:15]=1>C1COCC1>[NH2:9][C:10]1[C:11]([C:28]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:29])=[N:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH:25]([CH3:27])[CH3:26])(=[O:23])=[O:24])=[CH:20][CH:21]=2)=[CH:14][N:15]=1

Participants

4

Reactant 2

HCID 58084376HCID 58084376, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 54597164[3-Amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-phenyl-methanoneYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M Bromo(phenyl)magnesium in THF (823.2 μL, 0.8232 mmol) was added dropwise to a stirred solution of 3-amino-6-(4-isopropylsulfonylphenyl)-N-methoxy-N-methyl-pyrazine-2-carboxamide (100 mg, 0.2744 mmol) in anhydrous THF (6 mL) at −78° C. under an atmosphere of nitrogen. The reaction was stirred at this temperature for 30 minutes then allowed to warm to ambient temperature over 16 hours. The reaction mixture was concentrated in vacuo and residue was partitioned between DCM and water. The layers were separated and the organic extract was dried (MgSO4) and concentrated in vacuo. The material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å 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 as a yellow solid (49 mg, 42% Yield). NMR (400.0 MHz, DMSO) δ 1.16 (d, 6H), 3.44 (sept, 1H), 7.55-7.59 (m, 2H), 7.66 (m, 1H), 7.90 (d, 2H), 7.95-7.97 (m, 2H), 8.07 (br s, 2H), 8.18 (d. 2H) and 9.10 (s, 1H) ppm; (ES+) 382.0.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and residue
  2. customwas partitioned between DCM and water
  3. customThe layers were separated
  4. extractionthe organic extract
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  8. customThe fractions were collected
  9. customfreeze-dried

Sources & evidence

ORD record
ord-d2c8eaea58ce417b8b6b71b07bce6529
Source dataset
uspto-grants-2015_06
Patent number
US09062008B2

Reaction notes

Loading…