(2S,3S,4R,5R)-5-[6-[(2,2-Diphenylethyl)amino]-2-({4-[(trifluoroacetyl)amino]-1-piperidinyl}carbonyl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide → (2S,3S,4R,5R)-5-{2-[(4-amino-1-piperidinyl)carbonyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

HRID 10457Notes

Reaction equation

HRID 10457 reaction equation
[C:1]1([CH:7]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27]C(=O)C(F)(F)F)[CH2:23][CH2:22]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:34]2[O:38][C@H:37]([C:39]([NH:41][CH2:42][CH3:43])=[O:40])[C@@H:36]([OH:44])[C@H:35]2[OH:45])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.N>[NH2:27][CH:24]1[CH2:25][CH2:26][N:21]([C:19]([C:17]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[C@@H:34]3[O:38][C@H:37]([C:39]([NH:41][CH2:42][CH3:43])=[O:40])[C@@H:36]([OH:44])[C@H:35]3[OH:45])=[C:10]([NH:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:18]=2)=[O:20])[CH2:22][CH2:23]1

Participants

4

Reactant 1

HCID 58681715(2S,3S,4R,5R)-5-[6-[(2,2-Diphenylethyl)amino]-2-({4-[(trifluoroacetyl)amino]-1-piperidinyl}carbonyl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide

Product 1

HCID 60091694(2S,3S,4R,5R)-5-{2-[(4-amino-1-piperidinyl)carbonyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamideYield 101.7%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of (2S,3S,4R,5R)-5-[6-[(2,2-diphenylethyl)amino]-2-({4-[(trifluoroacetyl)amino]-1-piperidinyl}carbonyl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (Preparation 40) (40 mg, 0.056 mmol) in methanol (1 ml) and concentrated aqueous ammonia solution (0.5 ml) was stirred at room temperature for 48 hours. Solvent was removed by evaporation under reduced pressure to give the target compound as a white solid, (35 mg).

Workup

  1. customSolvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-dc41c535004c441f83b6625c12376dbc
Source dataset
uspto-grants-2006_08
Patent number
US07094769B2

Reaction notes

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