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 215878Notes

Reaction equation

HRID 215878 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.[Fe](Cl)(Cl)Cl>[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

5

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 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

The title compound can be prepared by dissolving N-{(1S,2R,3S,4R)-4-[6-(2,2-diphenylethylamino)-2-(4-nitro-pyrazol-1-yl)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-2-hydroxy-acetamide (Intermediate QD) in methanol and adding a 2:1 by mass mixture of activated carbon and iron (III) chloride (40 mol % with respect to the substrate), followed by a large excess (100-fold with respect to the substrate) of hydrazine monohydrate. The resulting mixture is stirred at 65° C. for 3 hours, then filtered, before being concentrated under reduced pressure. Trituration of the residue with petroleum ether and subsequent filtration would give the desired product as a colourless solid.

Workup

  1. additionadding a 2:1
  2. filtrationfiltered
  3. concentrationbefore being concentrated under reduced pressure
  4. filtrationTrituration of the residue with petroleum ether and subsequent filtration

Sources & evidence

ORD record
ord-9e75773647df4c68bbeaa49a9e85166b
Source dataset
uspto-grants-2012_06
Patent number
US08193164B2

Reaction notes

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