HCID 86667445, compound → (7S)-7-(2-chloro-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-one

HRID 75011Notes

Reaction equation

HRID 75011 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11]([CH2:19][C:20](OCC)=[O:21])([CH2:15][N+:16]([O-])=O)[CH2:10]2)[C:5]([F:25])=[CH:4][N:3]=1>CO.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:15][NH:16][C:20](=[O:21])[CH2:19]3)[CH2:10]2)[C:5]([F:25])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 86667445HCID 86667445, compound2×

Product 1

HCID 86667444(7S)-7-(2-chloro-5-fluoropyrimidin-4-ylamino)-2-azaspiro[4.5]decan-3-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-((3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-(nitromethyl)cyclohexyl)ethanoate, 62b, (1.60 g, 4.27 mmol) in MeOH (20 mL) was added Raney Nickel (0.03 g, 0.43 mmol). The reaction was shaken on a Parr apparatus at 40 psi of H2 overnight. The reaction was filtered, concentrated in vacuo and purified by silica gel chromatography (CH2Cl2:20% MeOH in CH2Cl2) to give 155 mg of 62c. LCMS+: 299.13 at 2.87 min (10-90% MeOH, 3/5 grad/run, Formic Acid).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography (CH2Cl2:20% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6db192047dcb41a3acd4be1b2de7687f
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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