(Diethylamino)sulfur trifluoride → HCID 58168929, compound

HRID 38800Notes

Reaction equation

HRID 38800 reaction equation
[N:1]1([C:7]([C:9]2[C:10]([C:27]([F:30])([F:29])[F:28])=[N:11][C:12]([NH:15][C:16]34[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:24][C:18](O)([CH2:19]5)[CH2:17]3)[CH2:23]4)=[N:13][CH:14]=2)=[O:8])[CH2:6][CH2:5]OC[CH2:2]1.C(N(S(F)(F)[F:37])CC)C.[C:40](=[O:43])([O-])O.[Na+]>ClCCl>[F:37][C:18]12[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][C:16]([NH:15][C:12]4[N:11]=[C:10]([C:27]([F:30])([F:29])[F:28])[C:9]([C:7]([N:1]5[CH2:2][CH2:40][O:43][CH2:5][CH2:6]5)=[O:8])=[CH:14][N:13]=4)([CH2:25]3)[CH2:17]1)[CH2:24]2

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 58168823HCID 58168823, compound

Product 1

HCID 58168929HCID 58168929, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-{[5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-yl]amino}adamantan-1-ol (150 mg) and dichloromethane (3 mL) was added diethylaminosulfur trifluoride (70 μL) under ice-cooling, followed by stirring at room temperature for 30 minutes. The reaction mixture was alkalified by adding a saturated aqueous sodium hydrogen carbonate solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain N-(3-fluoroadamantan-1-yl)-5-(morpholin-4-ylcarbonyl)-4-(trifluoromethyl)pyrimidin-2-amine (115 mg) as a white solid.

Workup

  1. temperaturecooling
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9816c2136a6e41f49026b8869fbec794
Source dataset
uspto-grants-2013_09
Patent number
US08524727B2

Reaction notes

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