HCID 59525963, compound → HCID 59526008, compound

HRID 385818Notes

Reaction equation

HRID 385818 reaction equation
[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[C:14]([F:15])=[CH:13][C:12]([C:16]([OH:19])([CH3:18])[CH3:17])=[CH:11][C:10]=2[F:20])[S:6][C:5]=1[NH:21][C:22]1[N:27]=[C:26]([C@@:28]2([OH:45])[CH2:33][CH2:32][N:31](C(OCC3C=CC=CC=3)=O)[CH2:30][C@@H:29]2[OH:44])[CH:25]=[CH:24][CH:23]=1)=[O:3].[H][H]>CO.[Pd]>[F:15][C:14]1[CH:13]=[C:12]([C:16]([OH:19])([CH3:18])[CH3:17])[CH:11]=[C:10]([F:20])[C:9]=1[C:7]1[S:6][C:5]([NH:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([C@@:28]3([OH:45])[CH2:33][CH2:32][NH:31][CH2:30][C@@H:29]3[OH:44])[N:27]=2)=[C:4]([C:2]([NH2:1])=[O:3])[CH:8]=1

Participants

5

Reactant 2

HCID 59525963HCID 59525963, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59526008HCID 59526008, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl (3S,4S)-4-[6-({3-(aminocarbonyl)-5-[2,6-difluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl]-3,4-dihydroxypiperidine-1-carboxylate (100 mg, 0.16 mmol) was dissolved in methanol (4.6 mL) and subjected to the H-cube hydrogenator machine, where the solution passed through a palladium on carbon cartridge at 0.5 mL/min at a temperature of 35° C. and a hydrogen pressure of 40 PSI. Once complete, the solution was concentrated and the crude residue was purified by reverse phase HPLC to yield the title compound.

Workup

  1. concentrationOnce complete, the solution was concentrated
  2. customthe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e6164ba674c84b41ae906109224c2c60
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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