HCID 71150049, compound → HCID 71150096, compound

HRID 1466238Notes

Reaction equation

HRID 1466238 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][NH:17][C:16](=[O:20])[CH:15]=2)=[CH:10][CH:9]=1)=[O:5]>C(O)C.CO.[Pd]>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]2)=[CH:12][CH:13]=1)=[O:5]

Participants

4

Reactant 1

HCID 71150049HCID 71150049, compound2×

Product 1

HCID 71150096HCID 71150096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumSolventHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

To a solution of 2,6-dimethyl-N-(4-(2-oxo-1,2-dihydropyridin-4-yl)benzyl)benzamide (see compound 5 of example 3B) in ethanol/methanol (5:1), 10% Pd/C was added and the mixture was hydrogenated (1 atm) at 23° C. for 12 hours. The catalyst was filtered through celite pad and washed with methanol Filtrate and washings were combined and the solvent was then concentrated and chromatographed (SiO2, 3-15% EtOAc/MeOH) to provide the title compound. MS found for C21H24N2O2 as (M+H)+337.1 1H NMR (400 MHz, dmso-d6): δ: 8.76 (t, J=5.6 Hz, 1H); 7.52 (brs, 1H), 7.27-7.14 (m, 4H); 7.13-6.99 (m, 3H); 4.40 (d, J=6.4 Hz, 2H); 3.23-3.16 (m, 2H); 3003-2.98 (m, 1H); 2.35-2.21 (m 2H); 2.17 (s, 6H); 1.88-1.78 (m, 2H).

Workup

  1. customat 23° C.
  2. customfor 12 hours
  3. filtrationThe catalyst was filtered through celite pad
  4. washwashed with methanol Filtrate and washings
  5. concentrationthe solvent was then concentrated
  6. customchromatographed (SiO2, 3-15% EtOAc/MeOH)

Sources & evidence

ORD record
ord-f5f7fb1b7ebd4b339e60e3c4f84bbae5
Source dataset
uspto-grants-2015_04
Patent number
US09000015B2

Reaction notes

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