Acetonitrile → HCID 67541052, compound

HRID 1026947Notes

Reaction equation

CS[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([NH:21][S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28].OO[S:43]([O-:45])=[O:44].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[C:54](#N)C>O>[CH3:54][S:43]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]([NH:21][S:22]([CH2:25][CH3:26])(=[O:23])=[O:24])=[O:20])=[C:14]2[N:13]=[CH:12][C:11]=1[C:27]([N:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)=[O:28])(=[O:45])=[O:44]

Participants

Conditions

Temperature: 40 °C

Procedure

N-[7-(2-Methylthiophenylamino)-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carbonyl]ethanesulfonamide (0.02 g, 0.03 mmol) obtained in Example 45, step 3 was dissolved in acetonitrile (1 mL) and water (0.5 mL), OXONE (0.05 mg, 0.08 mmol) was added, and the mixture was stirred at 40° C. for 1 hr. Aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give the title compound (0.02 g, 71%).

Workup

extractionthe mixture was extracted with chloroform
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record: ord-a1a84e93e84e4dcfa569cef3d3e3dc58
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729264B2

Reaction notes

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