HCID 86636958, compound → HCID 58000678, compound

HRID 1366486Notes

Reaction equation

HRID 1366486 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:35][C@@H:34]([OH:36])[C:33]([CH3:38])([CH3:37])[CH2:32]3)[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([O:12]CC2C=CC=CC=2)[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:35][C@@H:34]([OH:36])[C:33]([CH3:37])([CH3:38])[CH2:32]3)[N:27]=[C:26]([CH3:39])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86636958HCID 86636958, compound

Product 1

HCID 58000678HCID 58000678, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1606 g, 0.296 mmol) in MeOH (5 mL) was added 10% Pd/C (50% water, 48 mg). The mixture was hydrogenated under balloon pressure for 1 h, and was then filtered. The solution was concentrated in vacuo and the residue was crystallized from EtOAc-hexanes to afford [(2R)-2-(cyclopentylmethyl)-3-(2-{5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-2-methyl-4-pyrimidinyl}hydrazino)-3-oxopropyl]hydroxyformamide (0.1205 g, 90% yield) as a light pink solid. LCMS: (M+H)+: 453.3.

Workup

  1. filtrationwas then filtered
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was crystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-89632ec67b254d7088f9f435a452bae3
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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