(Diethylamino)sulfur trifluoride → HCID 68516223, compound

HRID 1717353Notes

Reaction equation

HRID 1717353 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]O)[CH:11]=2)=[O:6])[CH2:3][CH2:2]1.CCN(S(F)(F)[F:37])CC.C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[CH:14][C:13]=3[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][F:37])[CH:11]=2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68516636HCID 68516636, compound

Product 1

HCID 68516223HCID 68516223, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]-2-[(6-hydroxyhexyl)oxy]phenyl}-1H-1,2,3-triazole-4-carboxamide (0.14 g) obtained in Example 183 in dichloromethane (10 ml) was added DAST (0.10 ml) at −78° C. The reaction mixture was slowly allowed to warm to room temperature and stirred overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (ethyl acetate) and recrystallized from ethyl acetate-diisopropyl ether to give the title compound as a white powder (0.02 g, 15%).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column (ethyl acetate)
  5. customrecrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-277e80a7f12a45cd8225ad1fcf926b65
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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