Pyridine → N-(3-quinolinyl)quinoxaline-2-carboxamide Hydrochloride

HRID 2302057Notes

Reaction equation

HRID 2302057 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]([Cl:13])=[O:12].Cl.C[C@H:16]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1.[N:23]1[CH:28]=[CH:27]C=CC=1.[Cl:29][CH2:30]Cl>C(OCC)C>[ClH:13].[ClH:29].[N:22]1[C:19]2[C:20](=[CH:21][CH:16]=[CH:17][CH:18]=2)[CH:27]=[C:28]([NH:23][C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[O:12])[CH:30]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 2734681Quinoxaline-2-carbonyl chlorideHCID 178461307HCID 178461307, compound

Product 2

HCID 313Hydrochloric AcidHCID 22136337N-(3-quinolinyl)quinoxaline-2-carboxamide HydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-quinoxaloyl chloride (193 mg, 1 mmol) in dichloromethane (20 mL) was treated with trans-4-methylcyclohexylamine hydrochloride (150 mg, 1 mmol), and pyridine (0.2 mL) and stirred at ambient temperature for 60 min. After this time the reaction mixture was diluted with diethyl ether (50 mL), The organic solution was washed with 1 N NaOH (2×10 mL), brine (20 mL), dried over anhydrous MgSO4. Treatment with excess 1 M HCl in diethyl ether afforded 331 mg (98%) of 407:

Workup

  1. washThe organic solution was washed with 1 N NaOH (2×10 mL), brine (20 mL)
  2. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-d1b0fd812dd9468f95c3193a42070430
Source dataset
uspto-grants-2002_08
Patent number
US06429207B1

Reaction notes

Loading…