Sodium Carbonate → N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)urea

HRID 1168277Notes

Reaction equation

HRID 1168277 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([CH2:45][NH:46][C:47]([NH:49][CH2:50][CH2:51][N:52]([CH:56]1[CH2:60][CH2:59][CH2:58][CH2:57]1)[CH:53]([CH3:55])[CH3:54])=[O:48])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH:56]1([N:52]([CH:53]([CH3:54])[CH3:55])[CH2:51][CH2:50][NH:49][C:47]([NH:46][CH2:45][C:24]2[N:23]=[C:22]3[C:27]([N:28]=[CH:29][N:21]3[C@H:6]3[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]4[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=4)[O:7]3)=[C:26]([NH:30][CH2:31][CH:32]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[N:25]=2)=[O:48])[CH2:57][CH2:58][CH2:59][CH2:60]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 69978470(2R,3R,4R,5R)-4-(Acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)-amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl Acetate

Product 1

HCID 10305826N-{2-[Cyclopentyl(isopropyl)amino]ethyl}-N'-({6-[(2,2-diphenylethyl)amino]-9-[(2R,3R,4S,5R)-5-(2-ethyl-2H-tetrazol-5-yl)-3,4-dihydroxytetrahydro-2-furanyl]-9H-purin-2-yl}methyl)ureaYield 29.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(acetoxy)-2-{2-({[({2-[cyclopentyl(isopropyl)amino]ethyl}amino)carbonyl]amino}methyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 45) (135 mg, 0.16 mmol) and sodium carbonate (5 mg, 0.05 mmol) in methanol (5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:conc. aqueous ammonia (95:5:0.5 by volume) gradually changing to dichloromethane:methanol:conc. aqueous ammonia (90:10:1 by volume). Product containing fractions were evaporated and the resulting solid was dried under vacuum to afford the title compound as a white powder (35 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane
  3. additionProduct containing fractions
  4. customwere evaporated
  5. customthe resulting solid was dried under vacuum

Sources & evidence

ORD record
ord-ca367d2964cf4325b7d696f35d7fe974
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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