Ammonium Acetate → HCID 9805099, compound

HRID 1837384Notes

Reaction equation

HRID 1837384 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[CH2:29][N:30]2[CH2:35][CH2:34][C:33](=O)[CH2:32][CH2:31]2)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:43].[Na+]>CO.O>[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]=2[CH2:29][N:30]2[CH2:35][CH2:34][CH:33]([NH2:43])[CH2:32][CH2:31]2)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 54433960HCID 54433960, compound

Product 1

HCID 9805099HCID 9805099, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.477 g (1 mmol) of 3-(4-oxo-piperidin-1-ylmethyl)-2-phenyl-quinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (compound of Description 18), 0.462 g (6 mmol) of ammonium acetate were dissolved in 10 ml of methanol and stirred at room temperature for 1 h. Then 0.08 g of sodium cyanoborohydride were added and the mixture was stirred one night at room temperature. The reaction mixture was poured in 50 ml of water and the formed precipitate was filtered off. The aqueous phase was extracted with methylene chloride. The collected solid was dissolved in methylene chloride, both organic phases merged, washed with water, dried over MgSO4, concentrated to dryness. The residue was purified by micro flash chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 90/10/1) to afford 47 mg of the title compound as a white solid (yield ca 10%).

Workup

  1. stirringthe mixture was stirred one night at room temperature
  2. filtrationthe formed precipitate was filtered off
  3. extractionThe aqueous phase was extracted with methylene chloride
  4. dissolutionThe collected solid was dissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by micro flash chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 90/10/1)

Sources & evidence

ORD record
ord-0994c41c118343fdb35526d376edee75
Source dataset
uspto-grants-2004_08
Patent number
US06780875B2

Reaction notes

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