HCID 21973812, compound → HCID 21973814, compound

HRID 2085533Notes

Reaction equation

HRID 2085533 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])([CH3:13])[CH3:12])[C:5]([N+:18]([O-])=O)=[C:4]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1>C1(C)C=CC=CC=1>[NH2:18][C:5]1[C:4]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:3][C:2]([CH3:1])=[C:7]([CH3:8])[C:6]=1[NH:9][CH2:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])([CH3:12])[CH3:13]

Participants

3

Reactant 1

HCID 21973812HCID 21973812, compound

Product 1

HCID 21973814HCID 21973814, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-{2-[(2,3-dimethyl-5-nitro-6-phenoxypyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (2.40 g, 6.45 mmol) was dissolved in 20 mL of toluene and treated with 0.2 g of Pt (5% on carbon). The reaction mixture was then shaken under H2 (3 atm) for 24 h. Then reaction mixture was then treated with an additional 1.5 g of Pt (5% on carbon) and shaken an additional 8 h. The reaction mixture was then filtered through Celite, rinsing with toluene, and concentrated to give N-{2-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]-1,1-dimethylethyl}acetamide (1.80 g) as a colorless oil.

Workup

  1. customThen reaction mixture
  2. stirringshaken an additional 8 h
  3. filtrationThe reaction mixture was then filtered through Celite
  4. washrinsing with toluene
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77718b410fd4491b9cf41725a8dc6ad7
Source dataset
uspto-grants-2004_04
Patent number
US06720422B2

Reaction notes

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