Sodium Thiosulfate → HCID 52914151, compound

HRID 540767Notes

Reaction equation

HRID 540767 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:25]1[C:29]([O:30][C:31]2[CH:36]=[CH:35][C:34]([CH:37]([OH:39])[CH3:38])=[CH:33][CH:32]=2)=[CH:28][C:27]([C:40]2[CH:41]=[C:42]([C:46]([NH:49][S:50]([CH2:53][C:54]([F:57])([F:56])[F:55])(=[O:52])=[O:51])([CH3:48])[CH3:47])[CH:43]=[CH:44][CH:45]=2)=[N:26]1)[CH3:24].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][C:29]2[N:25]([CH2:23][CH3:24])[N:26]=[C:27]([C:40]3[CH:41]=[C:42]([C:46]([NH:49][S:50]([CH2:53][C:54]([F:55])([F:56])[F:57])(=[O:51])=[O:52])([CH3:47])[CH3:48])[CH:43]=[CH:44][CH:45]=3)[CH:28]=2)=[CH:36][CH:35]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 52914043HCID 52914043, compound

Product 1

HCID 52914151HCID 52914151, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (415 mg, 0.977 mmol, 2.00 equiv) was added to a solution of N-[1-(3-{1-ethyl-5-[4-(1-hydroxyethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (250 mg, 0.489 mmol, 1 equiv) in dichloromethane (4.9 mL) at 22° C. The reaction mixture was stirred for 2 hours, and then saturated aqueous sodium thiosulfate solution (3 mL) and saturated aqueous sodium bicarbonate solution (3 mL) were added. The biphasic mixture was stirred for 15 minutes, then was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, and the washed solution was dried over sodium sulfate. The dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash-column chromatography (hexanes, grading to 90% ethyl acetate-hexanes) to afford N-(1-{3-[5-(4-acetylphenoxy)-1-ethyl-1H-pyrazol-3-yl]phenyl}-1-methylethyl)-2,2,2-trifluoroethanesulfonamide (139 mg, 56%) Calcd (M+1)+: 510.2. Found: 510.1.

Workup

  1. stirringThe biphasic mixture was stirred for 15 minutes
  2. customwas partitioned between ethyl acetate and water
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialthe washed solution was dried over sodium sulfate
  5. filtrationThe dried solution was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash-column chromatography (hexanes, grading to 90% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-bf8d1be06e54479293aa16027fc0e47e
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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