Ethyl Acetate → 2-{4-[(3-Amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}ethanol

HRID 858375Notes

Reaction equation

HRID 858375 reaction equation
C(C1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]NC(NS(C3C=CC(C)=CC=3)(=O)=O)=O)=[CH:16][CH:15]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)C.C(OCC)(=[O:38])C>[Pd]>[NH2:4][C:5]1[C:6]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][OH:38])=[CH:18][CH:19]=2)=[N:7][C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 99353672-ETHYL-5,7-DIMETHYL-3-(4-{2-[({[(4-METHYLPHENYL)SULFONYL]AMINO}CARBONYL)AMINO]ETHYL}PHENYL)-3H-IMIDAZO[4,5-b]PYRIDINE

Product 1

HCID 218759922-{4-[(3-Amino-4,6-dimethyl-2-pyridinyl)amino]phenyl}ethanolYield 92%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of 2-{4-[(4,6-dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethanol (step 3, 1.6 g, 5.6 mmol) in ethyl acetate (15 mL) was added 10% Pd—C (160 mg). The mixture was stirred at room temperature for 6 h under hydrogen atmosphere. The palladium catalyst was removed by filtration and washed with ethanol (100 mL). The filtrate was concentrated under reduced pressure to afford 1.3 g (92%) of the title compound as pale yellow solids: 1H-NMR (CDCl3) δ 7.10 (4H, s), 6.61 (1H, s), 3.81 (2H, t, J=6.4 Hz), 2.80 (2H, t, J=6.4 Hz), 2.36 (3H, s), 2.19 (3H, s).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. washwashed with ethanol (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1bf8ba342a6a421d982f7e4d55d54b81
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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