HCID 86636999, compound → HCID 58000589, compound

HRID 1366600Notes

Reaction equation

HRID 1366600 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]([CH3:40])[CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[N:27]=[C:26]([CH3:41])[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].[C]>[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]([CH3:40])[CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[N:27]=[C:26]([CH3:41])[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 86636999HCID 86636999, compound

Product 1

HCID 58000589HCID 58000589, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

{(2R)-2-(Cyclopentylmethyl)-3-[2-(5-fluoro-2-methyl-6-{methyl[2-(4-pyridinyl)ethyl]amino}-4-pyrimidinyl)hydrazino]-3-oxopropyl}[(phenylmethyl)oxy]formamide (290 mg, 0.51 mmol) was dissolved in 10 mL of MeOH. 10% Pd/carbon (60 mg) was added, and the contents were stirred under a hydrogen balloon for approximately 5 h. The contents were then filtered to remove the catalyst, and the filtrate was concentrated in vacuo to provide {(2R)-2-(cyclopentylmethyl)-3-[2-(5-fluoro-2-methyl-6-{methyl[2-(4-pyridinyl)ethyl]amino}-4-pyrimidinyl)hydrazino]-3-oxopropyl}hydroxyformamide (230 mg, 96%). LCMS: (M+H)+: 474.3.

Workup

  1. filtrationThe contents were then filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1fbc8eb695a14bfc8ed39dbbadb1ca2b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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