Brimonidine → N-(4,5-dihydro-1H-imidazol-2-yl)-5-methylquinoxalin-6-amine

HRID 861305

반응식

HRID 861305 반응식
Br[C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2.[CH3:18][Sn](C)(C)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C)C=O>[CH3:18][C:2]1[C:11]([NH:12][C:13]2[NH:14][CH2:15][CH2:16][N:17]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[CH:5][CH:6]=[N:7]2

참가 물질

5

반응물 2

HCID 2435BrimonidineHCID 11661Tetramethyltin

생성물 1

HCID 185076N-(4,5-dihydro-1H-imidazol-2-yl)-5-methylquinoxalin-6-amine수율 56.8%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
145 °C

실험 절차

A sealable reaction tube was charged with 5-bromo-6-(2-imidazolin-2-ylamino) quinoxaline (104 mg., 0.36 mmol) (prepared as noted above), tetramethyl tin (214 mg., 1.2 mmol) and (Ph3P)2PdCl2 (10 mg) and dry dimethylformamide (2 ml) in a reaction tube. The reaction mixture was purged with dry nitrogen gas. The tube was sealed and heated to 145° C. for 6 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The dark brown residue was chromatographed (SiO2 ; 5/1 CHCl3 /CH3OH saturated with NH3 (g)) to yield 46.5 mg (53%) of the title compound as a light yellow solid. An analytical sample was prepared by recrystallization from CHCl3 /CH3OH and had a melting point of 183°-186° C. The title compound was characterized by 1H and 13CNMR, IR and mass spectral analysis.

후처리

  1. customThe reaction mixture was purged with dry nitrogen gas
  2. customThe tube was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent removed in vacuo
  5. customThe dark brown residue was chromatographed (SiO2 ; 5/1 CHCl3 /CH3OH saturated with NH3 (g))

출처 및 근거

ORD 기록
ord-3ff78ec8ede147fb96d12875dac71a79
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714486

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