Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-5-yl)carbamate → 5-amino-N-(4-isopropyl-3-methylphenyl)-6-oxo-1,6-dihydro-[3,4'-bipyridine]-2'-carboxamide

HRID 2283477Notes

Reaction equation

HRID 2283477 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[CH:18]=[C:17]([C:19]3[CH:24]=[C:23]([NH:25]C(=O)OCC4C=CC=CC=4)[C:22](=[O:36])[NH:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:6][C:5]=1[CH3:37])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:25][C:23]1[C:22](=[O:36])[NH:21][CH:20]=[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:2])[CH3:3])=[C:5]([CH3:37])[CH:6]=3)=[O:12])[CH:18]=2)[CH:24]=1

Participants

4

Reactant 1

HCID 118261436Benzyl (2'-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4'-bipyridin]-5-yl)carbamate

Product 1

HCID 1182507975-amino-N-(4-isopropyl-3-methylphenyl)-6-oxo-1,6-dihydro-[3,4'-bipyridine]-2'-carboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (2′-((4-isopropyl-3-methylphenyl)carbamoyl)-6-oxo-1,6-dihydro-[3,4′-bipyridin]-5-yl)carbamate (210 mg, 0.420 mmol) in MeOH (100 mL) was added Pd(OH)2/C (21 mg) and the mixture stirred overnight at RT under hydrogen. The Pd(OH)2/C was removed by filtration and the solvent evaporated to afford 5-amino-N-(4-isopropyl-3-methylphenyl)-6-oxo-1,6-dihydro-[3,4′-bipyridine]-2′-carboxamide (120 mg, 80% yield) as a grey solid: 1H NMR (400 MHz, CDCl3) δ 9.96 (s, 1H), 8.57 (s, 1H), 8.36 (s, 1H), 7.48 (s, 2H), 7.45 (s, 1H), 7.00 (d, J=2.8 Hz, 1H), 6.85 (s, 1H), 4.40 (s, 1H), 2.87-2.92 (m, 1H), 2.37 (s, 3H), 1.27 (d, J=6.8 Hz, 6H); MS (ES) m/z 363 (M+H).

Workup

  1. customThe Pd(OH)2/C was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-5cc10a01e3a24ee58804c98685da4a84
Source dataset
uspto-grants-2015_09
Patent number
US09145393B2

Reaction notes

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