Tert-butyl 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butylcarbamate → Tert-butyl 4-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]butylcarbamate

HRID 1064403Notes

Reaction equation

HRID 1064403 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:5]([N+:22]([O-])=O)=[C:4]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1>C1(C)C=CC=CC=1.C(O)(C)C.[Pd]>[NH2:22][C:5]1[C:4]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:3][C:2]([CH3:1])=[C:7]([CH3:8])[C:6]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 1

HCID 12109125Tert-butyl 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butylcarbamate

Product 1

HCID 12109126Tert-butyl 4-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]butylcarbamateYield 90.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent2×HCID 3776IsopropanolSolvent

Procedure

A solution of tert-butyl 4-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]butylcarbamate (7.32 g, 17.00 mmol) in a mixture of toluene (150 mL) and isopropanol (10 mL) was combined with a slurry of 10% palladium on carbon in toluene. The mixture was place under hydrogen pressure on a Parr apparatus for 24 hours. Additional catalyst was added at 1.5 hours (2.2 g) and 3 hours (3 g). The reaction mixture was filtered through a layer of Celite® filter agent to remove the catalyst. The layer of filter agent was washed with ethanol (1 L), ethanol/methanol (1 L), and methanol (1 L). The filtrate was concentrated under reduced pressure. The residue was combined with dichloromethane and heptane and then concentrated under reduced pressure to provide 6.17 g of tert-butyl 4-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]butylcarbamate as a sludgy brown yellow oil.

Workup

  1. customfor 24 hours
  2. additionAdditional catalyst was added at 1.5 hours (2.2 g) and 3 hours (3 g)
  3. filtrationThe reaction mixture was filtered through a layer of Celite®
  4. filtrationfilter agent
  5. customto remove the catalyst
  6. washThe layer of filter agent was washed with ethanol (1 L), ethanol/methanol (1 L), and methanol (1 L)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dfb5353464964067a8e4f68f578057bf
Source dataset
uspto-grants-2005_11
Patent number
US06969722B2

Reaction notes

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