Pyridine → HCID 178475436, compound

HRID 2236950Notes

Reaction equation

HRID 2236950 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 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-7a9008a6a8f04357bf201077609edc20
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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