2,5-Dimethoxytetrahydrofuran → HCID 178518368, compound

HRID 2236878Notes

Reaction equation

HRID 2236878 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7]/[CH:8]=[C:9]2\[C:10](=[O:21])[NH:11][C:12](=[O:20])[C:13]3[C:18]\2=[CH:17][C:16]([I:19])=[CH:15][CH:14]=3)=[CH:4][C:3]=1[OH:24].CO[CH:27]1[CH2:31][CH2:30][CH:29](OC)O1.Cl.ClC1C=CN=CC=1>CN(C)C=O>[OH:24][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:2]=1[N:1]1[CH:27]=[CH:31][CH:30]=[CH:29]1)[CH2:6][NH:7]/[CH:8]=[C:9]1\[C:10](=[O:21])[NH:11][C:12](=[O:20])[C:13]2[C:18]\1=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 818524-Chloropyridine hydrochlorideHCID 178507622HCID 178507622, compound

Product 1

HCID 178518368HCID 178518368, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4Z)-4-{[(4-amino-3-hydroxybenzyl)amino]methylene}-6-iodoisoquinoline-1,3(2H,4H)-dion (300 mg, 0.67 mmol), 2,5-dimethoxytetrahydrofuran (182.2 mg 1.4 mmol), and 4-chloropyridine hydrochloride (101 mg, 0.67 mmol) were placed in a flask and N,N-dimethylformamide (5 mL) is added. The mixture is then placed in a pre-heated oil bath at 80° C. for 2 hours. After cooling, all the solvent is evaporated. The brown solid is stirred in water and washed with ether to give the product as a brown solid 85 mg (25% yield).; mp 230-231° C.

Workup

  1. customwere placed in a flask
  2. temperatureAfter cooling
  3. customall the solvent is evaporated
  4. washwashed with ether

Sources & evidence

ORD record
ord-ab5f68fd2e584dc686955fb49f20f8f3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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