1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide → N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1-methylpiperidine-4-carboxamide

HRID 626507Notes

Reaction equation

HRID 626507 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][C:18]3[CH:19]=[N:20][C:21]([N+:24]([O-])=O)=[CH:22][CH:23]=3)[CH:14]=[CH:13][N:12]=2)=[O:9])[CH2:4][CH2:3]1>[Pd].CCOC(C)=O.CO>[NH2:24][C:21]1[N:20]=[CH:19][C:18]([O:17][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:8]([CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[O:9])[CH:16]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 904108531-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide

Product 1

HCID 90409884N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1-methylpiperidine-4-carboxamideYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide (0.20 g, 0.560 mmol) in 2:1 EtOAc/MeOH (15 mL) was treated with Palladium on carbon (50% wet) (0.066 g, 0.056 mmol) was hydrogenated (1 atm) overnight. The solids were removed via filtration through diatomaceous earth, washed with MeOH and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-1-methylpiperidine-4-carboxamide (130 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 10.43 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.77 (d, J=2.9 Hz, 1H), 7.60 (d, J=2.4 Hz, 1H), 7.26 (dd, J=8.9, 3.0 Hz, 1H), 6.63 (dd, J=5.7, 2.4 Hz, 1H), 6.51 (d, J=8.9 Hz, 1H), 6.01 (s, 2H), 2.77 (m, 2H), 2.39 (m, 1H), 2.14 (s, 3H), 1.83 (m, 2H), 1.67 (m, 2H), 1.57 (m, 2H); MS (ESI) m/z: 328.2 (M+H+).

Workup

  1. custom(1 atm) overnight
  2. customThe solids were removed via filtration through diatomaceous earth
  3. washwashed with MeOH
  4. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-f2c30d07b87048cea13471ab3d6e4579
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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