(Diethylamino)sulfur trifluoride → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-fluoropropyl)-1H-1,2,3-triazole-4-carboxamide

HRID 1717315Notes

Reaction equation

HRID 1717315 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=3)[C:11]=2[CH2:12][CH2:13][CH2:14]O)=[O:6])[CH2:3][CH2:2]1.C(N(S(F)(F)[F:33])CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:18][CH:17]=3)[C:11]=2[CH2:12][CH2:13][CH2:14][F:33])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 57665173HCID 57665173, compound

Product 1

HCID 57665104N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-fluoropropyl)-1H-1,2,3-triazole-4-carboxamideYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-hydroxypropyl)-1H-1,2,3-triazole-4-carboxamide (0.40 g) obtained in Example 113 in dichloromethane (4.5 ml) was added diethylaminosulfur trifluoride (0.18 ml) at −78° C. The reaction mixture was stirred for 5 hr while gradually heating to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=6/4 to ethyl acetate). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (0.024 g, 6%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column (hexane/ethyl acetate=6/4 to ethyl acetate)
  6. customThe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-153fcb7da13243ca97daa4572c67d975
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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