Dimethylformamide → HCID 22175619, compound

HRID 1797611Notes

Reaction equation

HRID 1797611 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:11](=[O:26])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15](Br)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2].[CH3:32][S-:33].[Na+].CN(C)C=O>O>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][C:9]1[N:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[C:11](=[O:26])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([S:33][CH3:32])=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 22175235HCID 22175235, compound

Product 1

HCID 22175619HCID 22175619, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of tert-butyl(6-bromo-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.24 g, 0.5 mmol), sodium thiomethoxide (0.080 g, 1.1 mmol) and N,N-dimethylformamide (4 mL) was stirred at 85° C. for 1 h, and the reaction mixture was poured into water (50 mL) and extracted twice with ethyl acetate (25 mL). The extracts were combined, washed with saturated aqueous sodium hydrogencarbonate (15 mL) and saturated brine (15 mL), dried over anhydrous magnesium sulfate (12 g) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v)) to give tert-butyl[2-isobutyl-6-(methylsulfanyl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.17 g, 73%) as a colorless powder.

Workup

  1. extractionextracted twice with ethyl acetate (25 mL)
  2. washwashed with saturated aqueous sodium hydrogencarbonate (15 mL) and saturated brine (15 mL)
  3. dry with materialdried over anhydrous magnesium sulfate (12 g)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1 (v/v))

Sources & evidence

ORD record
ord-293551028a6d4a27a819b923daa4f6f0
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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