Water → HCID 60206173, compound

HRID 1797642Notes

Reaction equation

HRID 1797642 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[C:40]([O:44][CH2:45][CH2:46][CH2:47][CH3:48])(=[O:43])[CH:41]=[CH2:42].C(=O)([O-])O.[Na+].O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[N:10]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:11](=[O:34])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[CH:16][C:15](/[CH:42]=[CH:41]/[C:40]([O:44][CH2:45][CH2:46][CH2:47][CH3:48])=[O:43])=[CH:14][CH:13]=2)=[O:39])([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 8846Butyl AcrylateHCID 516892Sodium BicarbonateHCID 22176315HCID 22176315, compound

Product 1

HCID 60206173HCID 60206173, compoundYield 24.2%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of tert-butyl[4-(4-chlorophenyl)-2-isobutyl-1-oxo-6-trifluoromethanesulfonyloxy-1,2-dihydro-3-isoquinolinyl]methylcarbamate (Example 186 (1)) (2.06 g, 3.5 mmol), butyl acrylate (0.76 ml, 5.3 mmol), sodium hydrogencarbonate (0.45 g, 5.3 mmol), tetrabutylammonium chloride (0.11 g, 0.4 mmol) and palladium acetate (0.09 g, 0.4 mmol) in N,N-dimethylformamide (20 ml) was stirred with heating at 100° C. under an argon atmosphere for 48 h. The reaction mixture was poured into water and extracted with ethyl acetate. After washing the extract with water, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give butyl (E)-3-[3-[[(tert-butoxycarbonyl)amino]methyl]-4-(4-chlorophenyl)-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenate (0.48 g, 23.8%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing the
  3. extractionextract with water
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9c967c84026b499c88228c58400aa5c3
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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