Toluene → N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]urea

HRID 897072노트

반응식

HRID 897072 반응식
[CH:1]([N:4]([CH:15]([CH3:17])[CH3:16])[CH2:5][CH2:6][NH:7][C:8](N1C=CN=C1)=[O:9])([CH3:3])[CH3:2].[NH2:18][CH2:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[C@H:29]2[C@H:33]([OH:34])[C@H:32]([OH:35])[C@@H:31]([CH2:36][OH:37])[O:30]2)=[C:22]([NH:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:21]=1.C1(C)C=CC=CC=1.C(O)(C)C>ClCCl>[OH:34][C@@H:33]1[C@H:32]([OH:35])[C@@H:31]([CH2:36][OH:37])[O:30][C@H:29]1[N:26]1[CH:25]=[N:24][C:23]2[C:27]1=[N:28][C:20]([CH2:19][NH:18][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:15]([CH3:17])[CH3:16])[CH:1]([CH3:2])[CH3:3])=[O:9])=[N:21][C:22]=2[NH:38][CH2:39][CH:40]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 3776IsopropanolHCID 21978296N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamideHCID 59875479(2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol

생성물 1

HCID 9874284N-({9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-N'-[2-(diisopropylamino)ethyl]urea수율 26.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N-[2-(Diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (84 mg, 0.35 mmol) (Preparation 27) was added to a stirred solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(hydroxymethyl)tetrahydro-3,4-furandiol (150 mg, 0.35 mmol) (Preparation 2) in dichloromethane (5 ml) at room temperature. The reaction was heated under reflux for 1 hour and then toluene (5 ml) and isopropanol (2 ml) were added. The dichloromethane was boiled off and the reaction was then heated under reflux for 1 hour. The reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume increasing to 80:20:2 by volume). This gave the title compound as a foam (60 mg).

후처리

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe reaction was then heated
  4. temperatureunder reflux for 1 hour
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-f2be0db4399f47debee49a2ab1e7b4c2
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921753B2

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