1h-imidazole-1-carboxamide → 9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-{2-[(([2-(1-piperidinyl)ethyl]amino}carbonyl)amino]ethyl}-9H-purine-2-carboxamide

HRID 353612노트

반응식

HRID 353612 반응식
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:15]=[C:14]2[C:10]([N:11]=[CH:12][N:13]2[C@H:16]2[C@H:20]([OH:21])[C@H:19]([OH:22])[C@@H:18]([CH2:23][OH:24])[O:17]2)=[C:9]([NH:25][CH2:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:8]=1)=[O:6].[N:40]1([C:45](N)=[O:46])[CH:44]=[CH:43][N:42]=[CH:41]1>C1(C)C=CC=CC=1.C(O)(C)C>[OH:21][C@@H:20]1[C@H:19]([OH:22])[C@@H:18]([CH2:23][OH:24])[O:17][C@H:16]1[N:13]1[CH:12]=[N:11][C:10]2[C:14]1=[N:15][C:7]([C:5]([NH:4][CH2:3][CH2:2][NH:1][C:45]([NH:40][CH2:44][CH2:43][N:42]1[CH2:20][CH2:19][CH2:18][CH2:23][CH2:41]1)=[O:46])=[O:6])=[N:8][C:9]=2[NH:25][CH2:26][CH:27]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

참가 물질

5

반응물 2

HCID 2653011h-imidazole-1-carboxamideHCID 60091691N-(2-Aminoethyl)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxamide

생성물 1

HCID 468865929-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-N-{2-[(([2-(1-piperidinyl)ethyl]amino}carbonyl)amino]ethyl}-9H-purine-2-carboxamide수율 145.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3776Isopropanol용매

실험 절차

N-(2-Aminoethyl)-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxamide (Preparation 17) (90 mg, 0.17 mmol) and N-[2-1-piperidinyl)ethyl]-1H-imidazole-1-carboxamide (Preparation 18) (40 mg, 0.18 mmol) were dissolved in a mixture of toluene (4 ml) and isopropanol (1 ml) and the solution heated under reflux for four hours. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (85:15:1.5, by volume). Product containing fractions were evaporated and the resulting solid triturated with diethyl ether, filtered and dried to afford the title compound as a white powder (85 mg).

후처리

  1. temperaturethe solution heated
  2. temperatureunder reflux for four hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with dichloromethane
  5. additionProduct containing fractions
  6. customwere evaporated
  7. customthe resulting solid triturated with diethyl ether
  8. filtrationfiltered
  9. customdried

출처 및 근거

ORD 기록
ord-2c0890ad28c74070b69cd26ecc8bfb89
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753322B2

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