Ammonia → HCID 68153574, compound

HRID 1946924Notes

Reaction equation

HRID 1946924 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:16]=[N:17][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:19][CH:20]=3)[NH:13][C:12](=S)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[NH3:25]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:15]3[CH:16]=[N:17][C:18]([O:21][CH:22]([F:24])[F:23])=[CH:19][CH:20]=3)[CH2:9][O:10][CH2:11][C:12]([NH2:25])=[N:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86668500HCID 86668500, compound

Product 1

HCID 68153574HCID 68153574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A dried pressure tube was charged under an argon atmosphere with a dispersion of 5-(3-bromo-phenyl)-5-(6-difluoromethoxy-pyridin-3-yl)-morpholine-3-thione (1.0 g) in a solution of ammonia (7M) in methanol (30 ml). The tube was sealed and heated at 100° C. for 3 hours. After cooling, the reaction mixture was evaporated to dryness and dissolved in dichloromethane, then loaded onto an SCX-cartridge. A 1:1-mixture of dichloromethane and methanol was passed through the column to remove impurities, and the aminoxazine was eluted with ammonia in methanol (2M solution). The (RS)-5-(3-bromo-phenyl)-5-(6-difluoromethoxy-pyridin-3-yl)-5,6-dihydro-2H-[1,4]oxazin-3-ylamine was obtained as a yellow foam (0.82 g, 83% of theory). MS (ISP): m/z=399 [M+H]+.

Workup

  1. customThe tube was sealed
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness
  4. dissolutiondissolved in dichloromethane
  5. customto remove impurities
  6. washthe aminoxazine was eluted with ammonia in methanol (2M solution)

Sources & evidence

ORD record
ord-430c7848ef3347248703c97483844001
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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