Potassium Carbonate → N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-2-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide

HRID 1504173노트

반응식

HRID 1504173 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(=[O:12])=[O:11])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][O:34][C:35]1[CH:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]([CH3:45])[C:40](=[O:46])[CH:39]=[CH:38]2>CN(C=O)C>[CH3:45][N:41]1[C:42]2[C:37](=[CH:36][C:35]([O:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][N:13]([CH2:14][CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])=[CH:44][CH:43]=2)[CH:38]=[CH:39][C:40]1=[O:46]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 465565342-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamideHCID 669600336-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one

생성물 1

HCID 70656815N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-2-nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide수율 96.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Nitro-N-(2-pyridin-3-ylethyl)benzenesulfonamide(308 mg), and potassium carbonate(276 mg) were added to a DMF solution(5 ml) of 6-(5-bromopentyloxy)-1-methyl-1H-quinolin-2-one(348 mg). The mixture was stirred at room temperature for 2 hours. Ice water was poured to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was washed with water, dried with anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate: methanol=10:1). The purified product was condensed to dryness under reduced pressure to give 5 the title compound(535 mg) as a yellow amorphous solid.

후처리

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with water
  3. dry with materialdried with anhydrous sodium sulfate, and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate: methanol=10:1)
  5. customcondensed to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-e515cf7d54664094af717775cb7f6b5a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212187B2

반응 노트

불러오는 중…