Ammonia → HCID 86685864, compound

HRID 1629774Notes

Reaction equation

HRID 1629774 reaction equation
[NH3:1].[C:2]1([CH3:27])[CH:7]=[CH:6][C:5]([C:8](=[O:26])/[CH:9]=[C:10](/[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:14][CH:13]=2)\[CH3:11])=[CH:4][CH:3]=1>CCO.CS(C)=O.CCOC(C)=O>[NH2:1][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][C:22]([F:24])([F:25])[F:23])=[CH:14][CH:13]=1)([CH3:11])[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:27])=[CH:3][CH:4]=1)=[O:26]

Participants

6

Reactant 2

HCID 222AmmoniaHCID 86685863HCID 86685863, compound

Product 1

HCID 86685864HCID 86685864, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonia was bubble into a solution of Intermediate 11D (1.34 mg, 0.64 mmol) in EtOH (20 mL) and DMSO (12 mL) for 10 min at 0° C. The reaction was stirred at rt overnight in a sealed pressure vessel. Analytical HPLC showed reaction to have progressed only ca. 10%. The mixture was cooled to −15° C., then ammonia was bubbled through for 7 min. The vessel was sealed and the reaction was stirred at rt overnight. Analytical HPLC showed the reaction to be ca. 25-30% complete. The mixture was diluted with EtOAc (75 mL), washed with water and sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to provide Intermediate 11E (281 mg, 20%) as a light brown oil. LCMS Anal. Calc'd for C21H24F3NO2 379.42, found [M+H] 380.3.

Workup

  1. customreaction
  2. temperatureThe mixture was cooled to −15° C.
  3. customammonia was bubbled through for 7 min
  4. customThe vessel was sealed
  5. stirringthe reaction was stirred at rt overnight
  6. customthe reaction
  7. washwashed with water
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-d1e57a4c64ff4858a3dff504a7680eeb
Source dataset
uspto-grants-2014_07
Patent number
US08791091B2

Reaction notes

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