Triethylamine → 2-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

HRID 1459509Notes

Reaction equation

HRID 1459509 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:18][C:19]1[CH:39]=[CH:38][C:22]([C:23]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]3[CH:35]=[CH:36][CH:37]=[C:27]3[CH2:26]2)=[O:24])=[CH:21][CH:20]=1>C(Cl)Cl>[CH:35]1[N:28]2[C:29]3[C:34]([N:25]([C:23]([C:22]4[CH:21]=[CH:20][C:19]([NH:18][C:4](=[O:5])[C:3]5[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=5[CH3:1])=[CH:39][CH:38]=4)=[O:24])[CH2:26][C:27]2=[CH:37][CH:36]=1)=[CH:33][CH:32]=[CH:31][CH:30]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 218370054,5-Dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline

Product 1

HCID 153406682-Methyl-N-[4-(pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1.5 mmol of 2-methylbenzoyl chloride in 10 ml of methylene chloride is added 3 mmol of triethylamine. After stirring for 15 minutes, 1.5 mmol of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline is added and the mixture stirred for 5 hours. The reaction mixture is washed with water, 1N HCl, NaHCO3, and brine. The reaction mixture is dried with Na2 SO4, filtered and evaporated in vacuo to give a solid which is purified by flash chromatography to give the desired product as a solid, m.p. 206°-207° C.

Workup

  1. stirringthe mixture stirred for 5 hours
  2. washThe reaction mixture is washed with water, 1N HCl, NaHCO3, and brine
  3. customThe reaction mixture is dried with Na2 SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a solid which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-692afb575d8746b085013b3fcb4a82a4
Source dataset
uspto-grants-1998_12
Patent number
US05854237

Reaction notes

Loading…