Tin tetrachloride → 3-amino-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide

HRID 446665

반응식

HRID 446665 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]([NH:22][S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-])=O)[CH:27]=3)(=[O:25])=[O:24])=[N:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Sn](Cl)(Cl)(Cl)Cl>O.CC(N(C)C)=O>[NH2:32][C:28]1[CH:27]=[C:26]([S:23]([NH:22][C:13]2[C:12]([NH:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)(=[O:24])=[O:25])[CH:31]=[CH:30][CH:29]=1

참가 물질

5

반응물 2

HCID 24287Tin tetrachlorideHCID 57448443N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)-3-nitrobenzenesulfonamide

생성물 1

HCID 574484483-amino-N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)benzenesulfonamide

시약·촉매·용매 2

HCID 962Water촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
80 °C

실험 절차

A flask was charged with N-(3-(3,5-dimethoxyphenylamino)quinoxalin-2-yl)-3-nitro-benzenesulfonamide (3.4 g, 7.06 mmol), prepared using procedures similar to those in Example 14, tin chloride solvate (6.4 g, 28.2 mmol), and 30 mL of DMA. A few drops of water were added and the reaction mixture was stirred at 80° C. for 3 hours, after which time, solvent was removed on a rotary evaporator, and 50 mL of water and 10 mL of Methanol were added. The slurry was filtered, and the filtrate was washed with MeOH, water, and diethyl ether (20 mL of each), resulting in 3.25 g 3-amino-N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)benzenesulfonamide. 1H NMR (400 MHz, DMSO) δ 12.2 (br s, 1H), 8.85 (s, 1H), 7.90 (br s, 1H), 7.50-7.60 (m, 1H), 7.3-7.4 (m, 4H), 7.2 (m, 3H), 6.74 (m, 1H), 6.24 (m, 1H), 5.56 (br s, 2H), 3.76 (s, 6H). MS (EI) m/z for C22H21N5O4S: 452.0 (MH+).

후처리

  1. customprepared
  2. customafter which time, solvent was removed on a rotary evaporator, and 50 mL of water and 10 mL of Methanol
  3. additionwere added
  4. filtrationThe slurry was filtered
  5. washthe filtrate was washed with MeOH, water, and diethyl ether (20 mL of each),
  6. customresulting in 3.25 g 3-amino-N-(3-(3,5-dimethoxy-phenylamino)quinoxalin-2-yl)benzenesulfonamide

출처 및 근거

ORD 기록
ord-b4191081e6af4864a7f3a35b5d5bb534
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481001B2

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