HCID 86730259, compound → HCID 86730258, compound

HRID 1850208Notes

Reaction equation

HRID 1850208 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([C:19]2[CH:41]=[CH:40][C:22]([CH2:23][N:24]3[CH2:29][CH2:28][N:27](C(OCC4C=CC=CC=4)=O)[CH2:26][CH2:25]3)=[CH:21][CH:20]=2)[CH3:18])[N:11]=1)([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([C:19]2[CH:41]=[CH:40][C:22]([CH2:23][N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:21][CH:20]=2)[CH3:18])[N:11]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86730259HCID 86730259, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86730258HCID 86730258, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 4-(4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzyl)piperazine-1-carboxylate (190 mg, 0.34 mmol) and 10% Pd—C(40 mg, 0.038 mmol) in ethanol (3.4 ml) is stirred under 1 atmosphere pressure of hydrogen for 3 h. The mixture is filtered and concentrated to give (S)-4-isopropyl-3-(2-(((S)-1-(4-(piperazin-1-ylmethyl)phenyl)ethyl)amino)pyrimidin-4-yl)oxazolidin-2-one as a white solid (97 mg, 67.2% yield).

Workup

  1. filtrationThe mixture is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-72da173d22c147ac8eddddd247ae99b2
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…