Dimethylformamide → HCID 178518278, compound

HRID 2236687Notes

Reaction equation

HRID 2236687 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]/OC.Cl.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1.CN(C)C=O.C(N(CC)CC)C>O1CCCC1.O>[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:18][CH2:19][C:20]1[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 574158824-(Aminomethyl)pyridin-2(1H)-one--hydrogen chloride (1/1)HCID 68692760(E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178518278HCID 178518278, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4E)-6-bromo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.26 g, 0.94 mmol) and 4-aminomethyl-1H-pyridin-2-one hydrochloride (0.15 g, 0.94 mmol) were coupled in tetrahydrofuran (5 mL) and N,N-dimethylformamide (3 mL) with triethylamine (0.28 g) at room temperature overnight. After the addition of water, the solid material is collected by Buchner filtration, washed with diethyl ether, water, and methanol, and dried under vacuum to give (4Z)-6-bromo-4-({[(2-oxo-1,2-dihydropyridin-4-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione (0.19 g, 54%) as a gray powder.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationthe solid material is collected by Buchner filtration
  4. washwashed with diethyl ether, water, and methanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8d6e454cc0a048a9adc2c189dafbf054
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…