(Diethylamino)sulfur trifluoride → N-Cyclopropyl-N-[1-(2-fluoro-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

HRID 1424538Notes

Reaction equation

HRID 1424538 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH:10]1([N:13]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34](O)([CH3:36])[CH3:35])[CH2:29][CH2:28]2)[C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][CH:24]=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:11]1.C([O-])(O)=O.[Na+]>ClCCl>[CH:10]1([N:13]([CH:27]2[CH2:32][CH2:31][N:30]([CH2:33][C:34]([F:7])([CH3:36])[CH3:35])[CH2:29][CH2:28]2)[C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][CH:24]=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 86709612N-Cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Product 1

HCID 73053140N-Cyclopropyl-N-[1-(2-fluoro-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (57 μL) is added drop wise to N-cyclopropyl-N-[1-(2-hydroxy-2-methyl-propyl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide (83 mg) in dry dichloromethane (12 mL) at −78° C. and the reaction mixture is stirred at this temperature for 2 h. The mixture is poured on aqueous NaHCO3 solution (15 mL) and the aqueous phase is extracted with dichloromethane. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The solid residue is triturated with diisopropyl ether, filtered off, and dried to give the title compound. LC (method 2): tR=1.10 min; Mass spectrum (ESI+): m/z =386 [M+H]+.

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe solid residue is triturated with diisopropyl ether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-f7f351e83b474d7882c82086ee1d49ac
Source dataset
uspto-grants-2015_01
Patent number
US08927726B2

Reaction notes

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