Ammonium formate → HCID 66631057, compound

HRID 1882621Notes

Reaction equation

HRID 1882621 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:48]2[CH:53]=[CH:52][C:51](Cl)=[CH:50][CH:49]=2)([OH:47])[CH2:9][NH:10][C:11]2[N:19]=[C:18]([N:20]3[CH2:24][CH2:23][C@@H:22]([NH:25][C:26]([NH:28][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:27])[CH2:21]3)[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][N:15]3[C@@H:35]2[CH2:39][C@H:38]([NH:40][C:41](=[O:44])[CH2:42][OH:43])[C@@H:37]([OH:45])[C@H:36]2[OH:46])=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:45][C@H:37]1[C@@H:36]([OH:46])[C@H:35]([N:15]2[CH:14]=[N:13][C:12]3[C:16]2=[N:17][C:18]([N:20]2[CH2:24][CH2:23][C@@H:22]([NH:25][C:26]([NH:28][C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[O:27])[CH2:21]2)=[N:19][C:11]=3[NH:10][CH2:9][C:8]([OH:47])([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)[CH2:39][C@@H:38]1[NH:40][C:41](=[O:44])[CH2:42][OH:43]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66630549HCID 66630549, compound

Product 1

HCID 66631057HCID 66631057, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of N-((1S,2R,3S,4R)-4-{6-[2,2-Bis-(4-chloro-phenyl)-2-hydroxy-ethylamino]-2-[(R)-3-(3-pyridin-3-yl-ureido)-pyrrolidin-1-yl]-purin-9-yl}-2,3-dihydroxy-cyclopentyl)-2-hydroxy-acetamide in ethanol is added 10 equivalents of ammonium formate and 20 mol % of 10% palladium on carbon. The mixture is stirred at 80° C. for five hours, allowed to cool and filtered through Celite™. Removal of the solvent under reduced pressure affords the title compound.

Workup

  1. temperatureto cool
  2. filtrationfiltered through Celite™
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f6132d62b575482db7fd4e8d2babdcc9
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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