Hydrazine hydrate (1:1) → N-{(1S,2R,3S,4R)-4-[2-(4-Amino-pyrazol-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

HRID 1882548Notes

Reaction equation

HRID 1882548 reaction equation
[C:1]1([CH:7]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([N:19]3[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[N:20]3)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:27]2[CH2:31][C@H:30]([NH:32][C:33](=[O:36])[CH2:34][OH:35])[C@@H:29]([OH:37])[C@H:28]2[OH:38])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>CO>[NH2:24][C:22]1[CH:21]=[N:20][N:19]([C:17]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[C@@H:27]3[CH2:31][C@H:30]([NH:32][C:33](=[O:36])[CH2:34][OH:35])[C@@H:29]([OH:37])[C@H:28]3[OH:38])=[C:10]([NH:9][CH2:8][CH:7]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:18]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66630082N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenyl-ethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Product 1

HCID 66630381N-{(1S,2R,3S,4R)-4-[2-(4-Amino-pyrazol-1-yl)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound is prepared by dissolving N-{(1S,2R,3S,4R)-4-[6-(2,2-Diphenyl-ethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate ZP2) in methanol (˜1.0M), adding a 2:1 mixture by weight of activated carbon and ferric chloride and an excess of hydrazine monohydrate, and stirring the resulting mixture at 65° C. for four hours. Filtration through Celite™, removal of the volatile components under reduced pressure, and purification by column chromatography/crystallisation, affords the title compound.

Workup

  1. customThe title compound is prepared
  2. filtrationFiltration
  3. customthrough Celite™, removal of the volatile components
  4. customunder reduced pressure, and purification
  5. customby column chromatography/crystallisation

Sources & evidence

ORD record
ord-619c46a5795f4dfcaec705708ecb379f
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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