(Diethylamino)sulfur trifluoride → HCID 90204727, compound

HRID 1480301Notes

Reaction equation

HRID 1480301 reaction equation
[CH:1]1([C:4]2[C:5]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:18](O)([CH3:20])[CH3:19])[C:14]([NH:16][CH3:17])=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CCN(S(F)(F)[F:34])CC>ClCCl>[CH:1]1([C:4]2[C:5]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:6][C:7]([C:10]([NH:12][CH:13]([C:18]([F:34])([CH3:20])[CH3:19])[C:14]([NH:16][CH3:17])=[O:15])=[O:11])=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 90204460HCID 90204460, compound

Product 1

HCID 90204727HCID 90204727, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-cyclopropyl-N-[3-hydroxy-3-methyl-1-(methylamino)-1-oxobutan-2-yl]-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide (example 236b, 75 mg, 193 μmol) in dry dichloromethane (2 ml) under an argon atmosphere was added DAST (38.8 mg, 31.8 μl, 241 μmol). The reaction mixture was stirred at room temperature overnight. The reaction was diluted with dichloromethane and extracted with a 1M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (25 mg, 33%). MS (ESI, m/z): 392.6 (M+H+).

Workup

  1. extractionextracted with a 1M aqueous solution of sodium bicarbonate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated down to dryness
  4. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-95e296f563aa45729c29888b09943b89
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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