(Diethylamino)sulfur trifluoride → HCID 52914041, compound

HRID 540764Notes

Reaction equation

HRID 540764 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([N:12]1[C:16]([O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)=[CH:15][C:14]([C:26]2[CH:27]=[C:28]([C:32]([NH:35][S:36]([CH2:39][C:40]([F:43])([F:42])[F:41])(=[O:38])=[O:37])([CH3:34])[CH3:33])[CH:29]=[CH:30][CH:31]=2)=[N:13]1)[CH3:11].C(=O)([O-])O.[Na+]>ClCCl>[CH2:10]([N:12]1[C:16]([O:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][F:7])=[CH:22][CH:23]=2)=[CH:15][C:14]([C:26]2[CH:27]=[C:28]([C:32]([NH:35][S:36]([CH2:39][C:40]([F:41])([F:43])[F:42])(=[O:38])=[O:37])([CH3:34])[CH3:33])[CH:29]=[CH:30][CH:31]=2)=[N:13]1)[CH3:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 52914040HCID 52914040, compound

Product 1

HCID 52914041HCID 52914041, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-ethyl-N-(trifluoro-λ4-sulfanyl)ethanamine (DAST, 0,021 mL, 0.16 mmol, 1.3 equiv) was added to a solution of N-[1-(3-{1-ethyl-5-[4-(hydroxymethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (62 mg, 0.13 mmol, 1 equiv) in dichloromethane (1.2 mL) at −78° C. The reaction mixture was stirred at −78° C. for 5 minutes, then saturated sodium hydrogencarbonate was added. The crude mixture was extracted with ethyl acetate. 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 50% ethyl acetate-hexanes) to afford N-[1-(3-{1-ethyl-5-[4-(fluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (22 mg, 35%). Calcd (M+1)+: 500.2. Found: 500.1.

Workup

  1. extractionThe crude mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialthe washed solution was dried over sodium sulfate
  4. filtrationThe dried solution was filtered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash-column chromatography (hexanes, grading to 50% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-77c5b35e91264b52ab4d7e562f30624f
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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