Triethylamine → N-[4-(Pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]-2,3-dichlorobenzamide

HRID 1598234노트

반응식

HRID 1598234 반응식
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]3[CH:18]=[CH:19][CH:20]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:30][C:31]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](Cl)=[O:34]>ClCCl>[CH:18]1[N:11]2[C:12]3[C:17]([N:8]([C:6]([C:5]4[CH:4]=[CH:3][C:2]([NH:1][C:33](=[O:34])[C:32]5[CH:36]=[CH:37][CH:38]=[C:39]([Cl:40])[C:31]=5[Cl:30])=[CH:22][CH:21]=4)=[O:7])[CH2:9][C:10]2=[CH:20][CH:19]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 179442,3-Dichlorobenzoyl chloride2회HCID 218370054,5-Dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline

생성물 1

HCID 21837108N-[4-(Pyrrolo[1,2-a]quinoxalin-5(4H)-ylcarbonyl)phenyl]-2,3-dichlorobenzamide수율 13.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

As described for Example 157, 0.47 g of 4,5-dihydro-5-(4-aminobenzoyl)pyrrolo[1,2-a]quinoxaline, 346 μl of triethylamine and 5 ml of dichloromethane are chilled (ice bath) and 0.415 g of 2,3-dichlorobenzoyl chloride in 2 ml of dichloromethane added. After stirring overnight, an additional 346 μl of triethylamine is added and an additional 0.415 g of 2,3-dichlorobenzoyl chloride added. The mixture is stirred for 2 hours, diluted with 50 ml of dichloromethane and the solution washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and filtered through a thin pad of hydrous magnesium silicate and the filtrate concentrated to dryness. The residue is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent to give 0.100 g of white solid, m.p. 230°-240° C.

후처리

  1. additionadded
  2. stirringThe mixture is stirred for 2 hours
  3. washthe solution washed with 20 ml each of H2O, 2N citric acid, 1M NaHCO3 and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered through a thin pad of hydrous magnesium silicate
  6. concentrationthe filtrate concentrated to dryness
  7. customThe residue is chromatographed on thick layer silica gel plates with ethyl acetate-hexane (1:1) as solvent

출처 및 근거

ORD 기록
ord-f07bf25338954ad89ad559f18bbd2570
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05736540

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