Water → HCID 22175275, compound

HRID 1797647Notes

Reaction equation

HRID 1797647 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]([NH2:26])=[S:25])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:34][C:35](=O)[CH3:36].C([O-])(=O)C.[Na+].O>C(O)C>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][C:9]1[N:10]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:11](=[O:27])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([C:24]1[S:25][CH:34]=[C:35]([CH3:36])[N:26]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11715BromoacetoneHCID 517045Sodium AcetateHCID 86592074HCID 86592074, compound

Product 1

HCID 22175275HCID 22175275, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of tert-butyl[6-(aminothiocarbonyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.46 g, 1 mmol), bromoacetone (0.20 g, 1.5 mmol) and sodium acetate (0.12 g, 1.5 mmol) in ethanol (10 ml) was refluxed under heating for 12 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl[4-butoxy-2-isobutyl-6-(4-methyl-1,3-thiazol-2-yl)-1-oxo-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.36 g, 73.5%) as an amorphous.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 12 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-18074154668543ccad216cb24ed92374
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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