Triethylamine → HCID 22405171, compound

HRID 441243Notes

Reaction equation

HRID 441243 reaction equation
[C:1]([CH2:4][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15](=[O:38])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:37])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[CH:18][CH:17]=2)[CH2:7][C:6]1=[O:39])([OH:3])=O.C(N(CC)CC)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:62][N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>ClCCl>[CH3:62][N:63]1[CH2:68][CH2:67][N:66]([C:1]([CH2:4][N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:15](=[O:38])[C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:37])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)=[CH:18][CH:17]=3)[CH2:7][C:6]2=[O:39])=[O:3])[CH2:65][CH2:64]1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 531671-MethylpiperazineHCID 73910Diphenylphosphinic chlorideHCID 22405038HCID 22405038, compound

Product 1

HCID 22405171HCID 22405171, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(carboxymethyl)-4-{4-[2-(4methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydro -quinoxalin-2-one (100 mg) in dichloromethane (10 ml) were added triethylamine (0.030 ml) and diphenylphosphinic chloride (54.7 mg) and the solution was stirred at ambient temperature for 30 minutes. Triethylamine (0.030 ml) and 1-methylpiperazine (0.032 ml) were added to the solution and the mixture was stirred at ambient temperature for 3 hours. The solution was washed with water and brine and dried over magnesium sulfate. The organic solution was evaporated in vacuo and the residue was subjected to a silica gel column (10 g, 2% methanol in chloroform). The object fractions were evaporated in vacuo and the residue was solidified with diethyl ether to give 1-[(4-methyl-1-piperazinyl)carbonylmethyl]-4-{4-[2-(4methylphenyl)benzoylamino]benzoyl}-1,2,3,4-tetrahydro -quinoxalin-2-one (77.0 mg) as a white powder.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 hours
  2. washThe solution was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe organic solution was evaporated in vacuo
  5. customThe object fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-710e76d2456341598f9ece590a26e053
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

Loading…