Ammonium formate → (1R,2S,3R,5S)-3-[6-(2,2-Diphenyl-ethylamino)-2-(piperidin 4-ylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoroacetate

HRID 1641926Notes

Reaction equation

HRID 1641926 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[N:30]=[C:29]3[C:25]([N:26]=[CH:27][N:28]3[C@@H:31]3[CH2:35][C@H:34]([N:36]4[CH:40]=[C:39]([CH2:41][OH:42])[CH:38]=[N:37]4)[C@@H:33]([OH:43])[C@H:32]3[OH:44])=[C:24]([NH:45][CH2:46][CH:47]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[N:23]=2)[CH2:17][CH2:16]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:54]1([CH:47]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:46][NH:45][C:24]2[N:23]=[C:22]([NH:21][CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[N:30]=[C:29]3[C:25]=2[N:26]=[CH:27][N:28]3[C@@H:31]2[CH2:35][C@H:34]([N:36]3[CH:40]=[C:39]([CH2:41][OH:42])[CH:38]=[N:37]3)[C@@H:33]([OH:43])[C@H:32]2[OH:44])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66737589(1R,2S,3R,5S)-3-[2-(1-Benzyl-piperidin-4-ylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoroacetate

Product 1

HCID 66736211(1R,2S,3R,5S)-3-[6-(2,2-Diphenyl-ethylamino)-2-(piperidin 4-ylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoroacetate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(1R,2S,3R,1S)-3-[2-(1-benzyl-piperidin-4-ylamino)-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-5-(4-hydroxymethyl-pyrazol-1-yl)-cyclopentane-1,2-diol trifluoroacetate (Example 78) (50 mg, 0.063 mmol) is dissolved in ethanol (2 ml). Palladium hydroxide (20% on carbon) (45 mg, 0.57 mmol) and ammonium formate (20 mg, 0.057 mmol) are added and the reaction mixture is refluxed for 1.5 hours. The reaction mixture is allowed to cool, the catalyst is filtered off and the solvent is removed in vacuo. The title compound is obtained after purification by reverse phase column chromatography (Isolute™ C18, 0-100% MeCN in water—0.1% TFA). MS (ES+) m/e 610 (MH+).

Workup

  1. temperaturethe reaction mixture is refluxed for 1.5 hours
  2. temperatureto cool
  3. filtrationthe catalyst is filtered off
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-da2095c5bb8e474a88bc01ad4ea4dd59
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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