Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate → Tert-butyl {4-butoxy-2-isobutyl-1-oxo-6-[2-(1,3-thiazol-4-yl)ethyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate

HRID 1797737Notes

Reaction equation

HRID 1797737 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15](/[CH:24]=[CH:25]/[C:26]1[N:27]=[CH:28][S:29][CH:30]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15]([CH2:24][CH2:25][C:26]1[N:27]=[CH:28][S:29][CH:30]=1)=[CH:14][CH:13]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 22175662Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate

Product 1

HCID 22175409Tert-butyl {4-butoxy-2-isobutyl-1-oxo-6-[2-(1,3-thiazol-4-yl)ethyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamateYield 97.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.21 g, 0.4 mmol) and 5% palladium carbon (0.2 g) in tetrahydrofuran (10 ml) was stirred under a hydrogen atmosphere at room temperature for 2 h. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[2-(1,3-thiazol-4-yl)ethyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.20 g, 95.2%) as crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-364f3700b8264b71aa5666a7f3b2c3a1
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…