Ammonia → HCID 86668087, compound

HRID 474117Notes

Reaction equation

HRID 474117 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C@@:8]2([CH:15]([F:17])[F:16])[NH:13][C:12](=S)[CH2:11][O:10][CH2:9]2)[C:5]([F:18])=[CH:4][CH:3]=1.[NH3:19]>CO.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([C@:8]2([CH:15]([F:17])[F:16])[CH2:9][O:10][CH2:11][C:12]([NH2:19])=[N:13]2)[C:5]([F:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86668088HCID 86668088, compound

Product 1

HCID 86668087HCID 86668087, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-5-(6-bromo-3-fluoro-pyridin-2-yl)-5-difluoromethyl-morpholin-3-thione (611 mg, 1.79 mmol) in methanol (15 ml) was added ammonia (5.12 ml, 35.8 mmol, 7M in methanol), the vial was sealed and the reaction mixture was stirred at rt for 20 h. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with aq. sodium thiosulfate solution (10%), water and brine, dried over sodium sulfate, filtered and evaporated. The crude product (640 mg) was chromatographed over silica gel (14 g, dichloromethane/methanol 95/5+0.5% NH3) to give the title compound. 180 mg (31% yield).

Workup

  1. customthe vial was sealed
  2. washThe organic layer was washed with aq. sodium thiosulfate solution (10%), water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (640 mg) was chromatographed over silica gel (14 g, dichloromethane/methanol 95/5+0.5% NH3)

Sources & evidence

ORD record
ord-f3394b817de7428281e79ec7f4bd5d27
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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