Hydrochloric Acid → HCID 86586705, compound

HRID 2088170Notes

Reaction equation

HRID 2088170 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([C:16]3[NH:17][CH:18]=[C:19]([S:21][CH3:22])[CH: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>C(OCC)C>[F:38][C:35]([F:36])([F:37])[C:27]1[CH:26]=[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@H:14]3[C:16]2[NH:17][CH:18]=[C:19]([S:21][CH3:22])[CH:20]=2)[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86586706HCID 86586706, compound

Product 1

HCID 86586705HCID 86586705, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]-methoxy}-6-[4-methylthioazol-2-yl]-1-phenyl-8-azabicyclo[3.2.1]octane (Example 78; 50 mg, 0.081 mmol) in diethyl ether (2 ml) was treated 1M etheral HCl (0.3 ml). The mixture was concentrated in vacuo. The residue was treated with 10% palladium on charcoal (180 mg) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° 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 purified by preparative TLC (dichloromethane:methanol) to give the title compound (15 mg, 35%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was treated with 10% palladium on charcoal (180 mg) ethanol (10 ml)
  3. customflushed with nitrogen gas
  4. filtrationfiltered through a pad of Celite™
  5. concentrationThe filtrate was concentrated
  6. custompurified by preparative TLC (dichloromethane:methanol)

Sources & evidence

ORD record
ord-5f2c923b945e4c3da0ee73c4d2a58a8c
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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