HCID 11641253, compound → HCID 11634118, compound

HRID 1261681Notes

Reaction equation

HRID 1261681 reaction equation
[CH:1]([C@:4]1([C:16]([N:18]2[CH2:23][CH:22]=[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH2:20][CH2:19]2)=[O:17])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([C@:4]1([C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH2:22][CH2:23]2)=[O:17])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11641253HCID 11641253, compound

Product 1

HCID 11634118HCID 11634118, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-((1R,3S)-3-isopropyl-3-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydropyridin-1(2H)-yl]carbonylcyclopentyl)tetrahydro-2H-pyran-4-amine (12.0 mg, 0.026 mmol) in methanol (1.0 mL) under N2 was added palladium (5.5 mg) (10% dry weight on wet activated carbon). The reaction mixture was stirred at room temperature under H2 (1 atm) overnight (22 h) and filtered through celite. The celite was washed with methylene chloride and the filtrate was concentrated to give the desired product (11.9 mg, 99%). MS calculated for C26H38F3N2O2: (M+H) 467.3; found 467.2.

Workup

  1. filtrationfiltered through celite
  2. washThe celite was washed with methylene chloride
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f55a563373c74282b627d5307ad730a4
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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