HCID 21913948, compound → Tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate

HRID 1008030Notes

Reaction equation

HRID 1008030 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:5]([N+:23]([O-])=O)=[C:4]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:3]=1>C(O)C.[Pt]>[NH2:23][C:5]1[C:4]([O:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:3][C:2]([CH3:1])=[C:7]([CH3:8])[C:6]=1[NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]

Participants

4

Reactant 1

HCID 21913948HCID 21913948, compound

Product 1

HCID 21913447Tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamateYield 78.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of of tert-butyl 2-{2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate (15.34 g, 34.35 mmol) in absolute ethanol (500 mL) was combined with 5% platinum on carbon (12.02 g) in a Parr vessel and placed under hydrogen pressure overnight. The reaction mixture was filtered through a layer of Celite® filter aid. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography (250 g of silica gel eluting with 1/1 ethyl acetate/hexanes) to provide 11.21 g of tert-butyl 2-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]ethoxy}ethylcarbamate.

Workup

  1. custompressure overnight
  2. filtrationThe reaction mixture was filtered through a layer of Celite®
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (250 g of silica gel eluting with 1/1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5e6fbaac18b4419fab6e5406e2cdf371
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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