2-Furancarboxylic acid → Furan-2-carboxylic acid (7-bromo-2,3-dimethoxy-quinoxalin-5-ylmethyl)-amide

HRID 1422230Notes

Reaction equation

HRID 1422230 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:17][CH3:18])[C:8]([O:15][CH3:16])=[N:9]2.[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](O)=[O:25].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C1COCC1>[Br:14][C:12]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:17][CH3:18])[C:8]([O:15][CH3:16])=[N:9]2)=[C:4]([CH2:3][NH:2][C:24]([C:20]2[O:19][CH:23]=[CH:22][CH:21]=2)=[O:25])[CH:13]=1

Participants

6

Reactant 3

HCID 69192-Furancarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18706309HCID 18706309, compound

Product 1

HCID 54513571Furan-2-carboxylic acid (7-bromo-2,3-dimethoxy-quinoxalin-5-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

300 mg (1 mmol) of 5-aminomethyl-7-bromo-2,3-dimethoxy-quinoxaline hydrochloride, 124 mg (1.1 equiv.) of furan-2-carboxylic acid, 212 mg (1.1 equiv.) of N-(3-dimethylaminopropyl)-N'-ethyl-carbodiimide hydrochloride and 12.2 mg (0.1 equiv.) of 4-dimethylamino-pyridine are stirred in dried THF at 20° C. for 20 hours. The mixture is poured onto water, and the solid is filtered off and washed with water and diethyl ether. After drying under a high vacuum, the title compound is obtained in the form of a beige solid.

Workup

  1. additionThe mixture is poured onto water
  2. filtrationthe solid is filtered off
  3. washwashed with water and diethyl ether
  4. customAfter drying under a high vacuum

Sources & evidence

ORD record
ord-43720819ff1b46c586146db278219114
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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