HCID 136360250, compound → HCID 136360249, compound

HRID 2088175Notes

Reaction equation

HRID 2088175 reaction equation
C([N:8]1[C@@H:13]2[C@@H:14]([C:16]3[NH:17][C:18](=[O:21])[NH:19][N:20]=3)[CH2:15][C@@:9]1([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:10]([O:22][CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd].C(O)C>[F:37][C:34]([F:35])([F:36])[C:26]1[CH:25]=[C:24]([CH2:23][O:22][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:15][C@@H:14]3[C:16]2[NH:17][C:18](=[O:21])[NH:19][N:20]=2)[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=1

Participants

4

Reactant 1

HCID 136360250HCID 136360250, compound

Product 1

HCID 136360249HCID 136360249, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2,4-dihydro-3H-1,2,4-triazol-3-on-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 86; 66 mg, 0.11 mmol), 10% palladium on charcoal (180 mg), ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +60° C. for 1.5 hour. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated to give the title compound. The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. customflushed with nitrogen gas
  2. filtrationfiltered through a pad of Celite™
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ea7cf1cf2fb14cd4a296ebd214121293
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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