Methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate → 6-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-[2-(4-isopropyl-1-piperidinyl)ethyl]-9H-purine-2-carboxamide

HRID 1060542Notes

Reaction equation

HRID 1060542 reaction equation
[C:1]1([CH:7]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([O:21]C)=O)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:23]2[C@H:27]([OH:28])[C@H:26]([OH:29])[C@@H:25]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])[O:24]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:41]([CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][CH2:51][NH2:52])[CH2:46][CH2:45]1)([CH3:43])[CH3:42]>>[NH3:9].[C:1]1([CH:7]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:52][CH2:51][CH2:50][N:47]3[CH2:48][CH2:49][CH:44]([CH:41]([CH3:43])[CH3:42])[CH2:45][CH2:46]3)=[O:21])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@H:23]2[C@H:27]([OH:28])[C@H:26]([OH:29])[C@@H:25]([C:30]([NH:32][CH2:33][CH3:34])=[O:31])[O:24]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 10187396Methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylateHCID 219783132-[4-(Propan-2-yl)piperidin-1-yl]ethan-1-amine

Product 2

HCID 222AmmoniaHCID 103053846-[(2,2-Diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-N-[2-(4-isopropyl-1-piperidinyl)ethyl]-9H-purine-2-carboxamideYield 123.3%

Procedure

Methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino) carbonyl]-3,4-dihydroxytetra-hydro-2-furanyl}-9H-purine-2-carboxylate (Preparation 11) (100 mg, 0.18 mmol) and 2-(4-isopropyl-1-piperidinyl)ethylamine (Preparation 17) (300 mg, 1.76 mmol) were heated at 120° C. under a nitrogen atmosphere for three hours. The reaction mixture was allowed to cool to room temperature and purified by column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (90:10:1 by volume) to afford the title compound as a white solid (76 mg, 62%).

Workup

  1. custompurified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-f7fc35a4d91047cbba0344703a7510fd
Source dataset
uspto-grants-2003_02
Patent number
US06525032B2

Reaction notes

Loading…