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 353612ノート

反応式

HRID 353612 の反応式
[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

参加物

5

反応物 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

生成物 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-carboxamide収率 145.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2c0890ad28c74070b69cd26ecc8bfb89
出典データセット
uspto-grants-2004_06
特許番号
US06753322B2

反応ノート

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