HCID 59472088, compound → HCID 59472367, compound

HRID 78651Notes

Reaction equation

HRID 78651 reaction equation
[NH2:1][C:2]1[C:3]([C:20]([NH:22][NH:23][C:24]([NH2:26])=S)=[O:21])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1>ClCCCl>[NH2:1][C:2]1[C:3]([C:20]2[O:21][C:24]([NH2:26])=[N:23][N:22]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

3

Reactant 1

HCID 59472088HCID 59472088, compound

Product 1

HCID 59472367HCID 59472367, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

EDC (109.3 mg, 0.5704 mmol) was added to a stirred suspension of [[3-amino-6-(4-isopropylsulfonylphenyl)pyrazine-2-carbonyl]amino]thiourea (150 mg, 0.3803 mmol) in DCE (3.000 mL) and the reaction mixture heated at reflux for 22 h. The solvent was removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3×10 mL) and the combined organic extracts dried MgSO4, filtered and concentrated in vacuo to give the sub-title compound as a yellow solid (118 mg, 86%) 1H NMR (400 MHz, DMSO) d 1.19 (d, 6H), 3.45 (dt, 1H), 7.65-7.80 (m, 4H), 7.95 (d, 2H), 8.26 (d, 2H) and 8.89 (s, 1H) ppm; MS (ES+) 361.0

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 22 h
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  6. filtrationthe combined organic extracts dried MgSO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f7030a3e13745efa0d772823a8477cf
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

Loading…