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

HRID 1826901Notes

Reaction equation

HRID 1826901 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-b80a9b23ab354b16a79069278e8a9fee
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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