HCID 68927819, compound → HCID 57938748, compound

HRID 1044610Notes

Reaction equation

HRID 1044610 reaction equation
[CH:1]([C@:4]1([C:18]([N:20]2[CH2:25][CH:24]=[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH2:22][CH2:21]2)=[O:19])[CH2:8][CH2:7][C@@H:6]([NH:9][C@@H:10]2[CH2:15][CH2:14][O:13][CH2:12][CH:11]2[O:16][CH3:17])[CH2:5]1)([CH3:3])[CH3:2]>CO>[CH:1]([C@:4]1([C:18]([N:20]2[CH2:21][CH2:22][CH:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=3)[CH2:24][CH2:25]2)=[O:19])[CH2:8][CH2:7][C@@H:6]([NH:9][C@@H:10]2[CH2:15][CH2:14][O:13][CH2:12][CH:11]2[O:16][CH3:17])[CH2:5]1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68927819HCID 68927819, compound

Product 1

HCID 57938748HCID 57938748, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4R)-N-((1R,3S)-3-Isopropyl-3-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydropyridin-1(2H)-yl]carbonylcyclopentyl)-3-methoxytetrahydro-2H-pyran-4-amine (8.0 mg, 0.016 mmol) was dissolved in methanol (0.63 mL), degassed-purged with N2, followed by the addition of Palladium (3.44 mg) (10% dry weight on wet activated carbon). The reaction flask was degassed-purged with N2 three times, then stirred at room temperature under H2 (1 atm) overnight. The mixture was filtered through celite pad, washed with methylene chloride and concentrated to provide the desired product as a white solid (5.7 mg, 71%). LC-MS calculated for C27H40F3N2O3: (M+H) 497.2; found 497.2.

Workup

  1. customdegassed-purged with N2
  2. additionfollowed by the addition of Palladium (3.44 mg) (10% dry weight on wet activated carbon)
  3. customThe reaction flask was degassed-purged with N2 three times
  4. filtrationThe mixture was filtered through celite pad
  5. washwashed with methylene chloride
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2031cf6a572543ba9a776f6b9eb35f65
Source dataset
uspto-grants-2013_10
Patent number
US08563582B2

Reaction notes

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