Pyrazole → 1-Pyrazol-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513757Notes

Reaction equation

HRID 513757 reaction equation
CC([O-])(C)C.[K+].[NH:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.Cl[C:13]1[C:30]2[C:17](=[C:18]3[C:27](=[CH:28][CH:29]=2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:20](=[O:32])(=[O:31])[NH:19]3)[N:16]=[CH:15][CH:14]=1>CS(C)=O>[N:7]1([C:13]2[C:30]3[C:17](=[C:18]4[C:27](=[CH:28][CH:29]=3)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[S:20](=[O:31])(=[O:32])[NH:19]4)[N:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 23665647Potassium tert-butoxideHCID 681833551-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Product 1

HCID 681832231-Pyrazol-1-yl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxideYield 29%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOtBu (76 mg, 0.68 mmol) was added to a solution of pyrazole (51 mg, 0.76 mmol) in DMSO (1 ml) at 0° C. in a sealed tube and the mixture was stirred at room temperature for 15 min. 1-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 305 (80 mg, 0.252 mmol) was added and the mixture was heated at 100° C. for 4 h. After cooling, the mixture was poured onto ice and the aqueous was extracted with iPA: chloroform (30:70). The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with chloroform/MeOH (98:2) to give the title compound (25 mg, 29%).

Workup

  1. temperaturethe mixture was heated at 100° C. for 4 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto ice
  4. extractionthe aqueous was extracted with iPA
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with chloroform/MeOH (98:2)

Sources & evidence

ORD record
ord-baedf271d1ef4a26a21424463f225fe2
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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