p-Cyanobenzyl alcohol → 4-cyanobenzyl Isoquinolin-5-ylcarbamate

HRID 585919

Reaction equation

HRID 585919 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1)#[N:2].[N:11]([C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][N:18]=[CH:19]2)=[C:12]=[O:13]>C(OCC)C>[CH:19]1[C:20]2[C:15](=[C:14]([NH:11][C:12](=[O:13])[O:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][N:18]=1

Participants

4

Reactant 2

HCID 160549p-Cyanobenzyl alcoholHCID 115863575-Isocyanatoisoquinoline

Product 1

HCID 99722244-cyanobenzyl Isoquinolin-5-ylcarbamateYield 44%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Cyanobenzyl alcohol (150 mg, 1.13 mmol) in diethyl ether (10 mL) was treated with the product from Example 61A as an ethereal solution. The mixture was stirred for 2 hours, filtered, and the filter cake was washed with diethyl ether to provide the title compound as an off-white solid (150 mg, 44%). 1H NMR (300 MHz, DMSO-d6) δ 9.95 (s, 1H), 9.32 (d, J=1.0 Hz, 1H), 8.52 (d, J=6.1 Hz, 1H), 7.88-7.99 (m, 5H), 7.65-7.70 (m, 3H), 5.31 (s, 2H); MS (ESI+) m/z 304 (M+H)+.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with diethyl ether

Sources & evidence

ORD record
ord-74e6e9434d0e4f29b38ba8cc700bc19f
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Linked notes

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