Pyridine → HCID 178431209, compound

HRID 2236951Notes

Reaction equation

HRID 2236951 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][CH2:16][C:17]1[CH:27]=[C:26]([OH:28])[C:20]2[O:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[CH:18]=1.N1C=CC=CC=1.[CH:35]1([C:38](Cl)=[O:39])[CH2:37][CH2:36]1>CN(C)C=O>[CH:35]1([C:38]([O:28][C:26]2[C:20]3[O:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=3[CH:18]=[C:17]([CH2:16][NH:15]/[CH:14]=[C:5]3\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]4[C:4]\3=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=4)[CH:27]=2)=[O:39])[CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 178431207HCID 178431207, compound

Product 1

HCID 178431209HCID 178431209, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4Z)-6-bromo-4-({[(7-hydroxy-2,2-dimethyl-1,3-benzodioxol-5-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione (30 mg, 67 μmol) in dimethylformamide (0.5 mL) is added pyridine (12 μL, 0.17 mmol) and cyclopropanecarbonyl chloride (10 μL). The reaction mixture is shaken overnight at room temperature and then purified by reverse-phase high performance liquid chromatography to give 6-({[(Z)-(6-bromo-1,3-dioxo-2,3-dihydroisoquinolin-4(1H)-ylidene)methyl]amino}methyl)-2,2-dimethyl-1,3-benzodioxol-4-yl cyclopropanecarboxylate.

Workup

  1. custompurified by reverse-phase high performance liquid chromatography

Sources & evidence

ORD record
ord-a6d226dd1f8c43dabeda7b18f004ba91
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…