Triethylamine → N-[2-(1H-imidazol-1-yl)ethyl]adenosine, hydrochloride

HRID 345168

반응식

HRID 345168 반응식
[CH:1]1[N:6]=[C:5]([Cl:7])[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[N:20]1([CH2:25][CH2:26][NH2:27])[CH:24]=[CH:23][N:22]=[CH:21]1.C(N(CC)CC)C>C(O)C>[ClH:7].[N:20]1([CH2:25][CH2:26][NH:27][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[CH:24]=[CH:23][N:22]=[CH:21]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 4306672-(1H-imidazol-1-yl)ethanamine

생성물 1

HCID 9930713N-[2-(1H-imidazol-1-yl)ethyl]adenosine, hydrochloride수율 59%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 6-chloropurine riboside (1.63 g, 5.69 mmol) in 12 ml of absolute ethanol was added 0.63 g (5.7 mmol) of 2-(imidazol-1-yl)ethylamine (prepared in accordance with Z.Obsch. Chem. 9 1933 (1939); Chem Ab. 1940 2466) plus 0.80 g (8.0 mmol) of triethylamine. The reaction mixture was heated under reflux for 77 hours. Removal of the solvent in vacuo and chromatography of the residue on silica gel eluting with a mixture of MeOH (NH3) and dichloromethane in a ratio of 14:86 gave the free base of the title compound in an amount of 1.2 g (59% yield). The material was converted to the hydrochloride salt by suspending the material in 20 ml of water at 0° centigrade and adding 1N hydrochloric acid until a pH of 2.6 was attained. The solution was frozen and lyophilized to a white powder which was passed through a column of cellulose powder eluting with a mixture of 85 parts n-butanol and 15 parts water. The appropriate fractions were combined and concentrated to give a glass which was azeotroped twice with water and then dissolved in water, frozen and lyophilized yielding 0.97 g of the title compound (41% yield) as a white powder.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 77 hours
  3. customRemoval of the solvent in vacuo and chromatography of the residue on silica gel eluting
  4. additionwith a mixture of MeOH (NH3) and dichloromethane in a ratio of 14:86

출처 및 근거

ORD 기록
ord-43fb8a2a8fb04b489381b4b7dd184e51
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055569

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