HCID 59145887, compound → HCID 59145886, compound

HRID 887770Notes

Reaction equation

HRID 887770 reaction equation
C([N:8](CC1C=CC=CC=1)[C:9]1[N:14]=[C:13]2[CH:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:17][C:12]2=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(=O)C.[OH-].[Pd+2].[OH-].[C]>[NH2:8][C:9]1[N:14]=[C:13]2[CH:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH2:16][CH2:17][C:12]2=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59145887HCID 59145887, compound

Product 1

HCID 59145886HCID 59145886, compoundYield 7.4%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

(N-{2-[2-(Dibenzylamino)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl]ethyl}acetamide (870 mg, 2.18 mmol) was dissolved in acetic acid (22 mL), 20% palladium hydroxide-carbon powder (220 mg) was added, and the mixture was stirred under a hydrogen atmosphere at room temperature for 20 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure, diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. This was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (35.3 mg, yield 7%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialThis was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ca7a133878604e5b9a44c7b21c6ab8c7
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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