Hydrochloric Acid → HCID 86586776, compound

HRID 2088226Notes

Reaction equation

HRID 2088226 reaction equation
C([N:8]1[C@@H:13]2[C@:14]([F:22])([C:16]3[N:17]=[N:18][N:19]([CH3:21])[N:20]=3)[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1.Cl>>[F:33][C:31]([F:32])([F:34])[C:29]1[CH:30]=[C:25]([CH2:24][O:23][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:15][C@@:14]3([F:22])[C:16]2[N:17]=[N:18][N:19]([CH3:21])[N:20]=2)[CH:26]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:28]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86586775HCID 86586775, compound

Product 1

HCID 86586776HCID 86586776, compoundYield 82%

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]-methoxy}-6-fluoro-6-(2-methyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 173b; 74 mg, 0.12 mmol) was treated with an etheral solution of hydrogen chloride and concentrated. The residue was dissolved in ethanol (20 ml) and 10% palladium on charcoal (109 mg) was added. The mixture was stirred under hydrogen atmosphere (1 atm) at +60° C. for 30 minutes. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated and the residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia) to give the title compound (52 mg, 82%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethanol (20 ml)
  3. addition10% palladium on charcoal (109 mg) was added
  4. customflushed with nitrogen gas
  5. filtrationfiltered through a pad of Celite™
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by chromatography on silica gel (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-403fea6147ae46ec965777c53ab0e8d0
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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