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

HRID 1292061ノート

反応式

HRID 1292061 の反応式
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

参加物

5

反応物 2

HCID 2435BrimonidineHCID 11661Tetramethyltin

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
145 °C

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-d49e13038d414964b2fb515cd191611b
出典データセット
uspto-grants-1998_05
特許番号
US05756503

反応ノート

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