Pyridine → HCID 178475436, compound

HRID 2236729Notes

Reaction equation

HRID 2236729 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.[C:35](Cl)(=[O:37])[CH3:36]>CN(C)C=O>[C:35]([O:28][C:26]1[C:20]2[O:21][C:22]([CH3:25])([CH3:24])[O:23][C:19]=2[CH:18]=[C:17]([CH2:16][NH:15]/[CH:14]=[C:5]2\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]3[C:4]\2=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH:27]=1)(=[O:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 178431207HCID 178431207, compound

Product 1

HCID 178475436HCID 178475436, 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 N,N-dimethylformamide (0.5 mL) is added pyridine (12 μL, 0.17 mmol) and acetyl 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 acetate.

Workup

  1. custompurified by reverse-phase high performance liquid chromatography

Sources & evidence

ORD record
ord-c20332ebfb1b42a78f09596c06454fbb
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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