Water → HCID 69152679, compound

HRID 1986469Notes

Reaction equation

HRID 1986469 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:45][CH:46]([CH3:48])[CH3:47])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([NH:27]C(=O)OCC1C3C=CC=CC=3C3C1=CC=CC=3)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1.O>CN(C)C=O>[NH2:27][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH2:45][CH:46]([CH3:48])[CH3:47])[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[C:19]2[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 68833740HCID 68833740, compound

Product 1

HCID 69152679HCID 69152679, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9H-fluoren-9-ylmethyl 3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-4-(4-methylphenyl)-6-quinolinylcarbamate (1.28 g, 2.0 mmol) in N,N-dimethylformamide (20 ml) was added piperidine (1 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium-sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give tert-butyl [6-amino-2-isobutyl-4-(4-methylphenyl)-3-quinolinyl]methylcarbamate (0.81 g, yield 96.4%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium-sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb3543dde3a94192973361e4f958ce91
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

Loading…