HCID 68927819, compound → HCID 57938748, compound

HRID 1436805Notes

Reaction equation

HRID 1436805 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-((1 R,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-54c55398f5d74f6491d326cd10accab6
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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