HCID 59472088, compound → HCID 59472367, compound

HRID 2204869Notes

Reaction equation

HRID 2204869 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-bd908e14edd14662804de221055f0c93
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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