Potassium Carbonate → N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(4-nitro-imidazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

HRID 2382398Notes

Reaction equation

HRID 2382398 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17]([CH2:19][O:20]C(=O)C)=[O:18])[C@@H:13]([OH:24])[C@H:12]2[OH:25])=[C:4]([NH:26][CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[N+:47]([C:50]1[N:51]=[CH:52][NH:53][CH:54]=1)([O-:49])=[O:48]>CN1CCCC1=O.C(OCC)(=O)C>[C:35]1([CH:28]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:27][NH:26][C:4]2[N:3]=[C:2]([N:53]3[CH:54]=[C:50]([N+:47]([O-:49])=[O:48])[N:51]=[CH:52]3)[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:18])[CH2:19][OH:20])[C@@H:13]([OH:24])[C@H:12]2[OH:25])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 86637573Acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl esterHCID 178526856HCID 178526856, compound

Product 1

HCID 66631134N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(4-nitro-imidazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

The title compound is prepared by dissolving acetic acid {(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentylcarbamoyl}-methyl ester (Intermediate Q1) in N-methyl-2-pyrrolidinone, followed by potassium carbonate (5 equivalents) and 4-nitro-1H-imidazole (10 equivalents). The mixture is heated by microwave irradiation to 150° C. for two hours, then diluted with ethyl acetate and washed consecutively with water (×2) and brine, before drying over magnesium sulfate. Filtration, removal of the volatile components under reduced pressure and purification by flash column chromatography/crystallisation affords the title compound.

Workup

  1. customThe title compound is prepared
  2. washwashed consecutively with water (×2) and brine
  3. dry with materialbefore drying over magnesium sulfate
  4. filtrationFiltration, removal of the volatile components
  5. customunder reduced pressure and purification
  6. customby flash column chromatography/crystallisation

Sources & evidence

ORD record
ord-0dff6e0370da4b93a862fcc9872b13bf
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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