(Diethylamino)sulfur trifluoride → HCID 52914150, compound

HRID 540766Notes

Reaction equation

HRID 540766 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]([CH:24](O)[CH3:25])=[CH:20][CH:19]=2)=[CH:15][C:14]([C:27]2[CH:28]=[C:29]([C:33]([NH:36][S:37]([CH2:40][C:41]([F:44])([F:43])[F:42])(=[O:39])=[O:38])([CH3:35])[CH3:34])[CH:30]=[CH:31][CH:32]=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]([CH:24]([F:7])[CH3:25])=[CH:22][CH:23]=2)=[CH:15][C:14]([C:27]2[CH:28]=[C:29]([C:33]([NH:36][S:37]([CH2:40][C:41]([F:42])([F:44])[F:43])(=[O:39])=[O:38])([CH3:35])[CH3:34])[CH:30]=[CH:31][CH:32]=2)=[N:13]1)[CH3:11]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 52914043HCID 52914043, compound

Product 1

HCID 52914150HCID 52914150, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

N-ethyl-N-(trifluoro-λ4-sulfanyl)ethanamine (DAST, 0.020 mL, 0.15 mmol, 1.3 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 (62 mg, 0.12 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-(1-fluoroethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)-1-methylethyl]-2,2,2-trifluoroethanesulfonamide (40 mg, 64%). Calcd (M+1)+: 514.2. Found: 514.1.

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-daf78148a5f346e6b3d7839badcd3873
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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