N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide → N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

HRID 626501Notes

Reaction equation

HRID 626501 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:21]([O-])=O)[N:3]=1>[Pd].CCOC(C)=O.CO>[NH2:21][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 90410595N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 90409528N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamideYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (0.50 g, 1.591 mmol) in 2:1 EtOAc/MeOH (30 mL) was treated with palladium on carbon (50% wet, 0.188 g, 0.159 mmol) and hydrogenated (1 atm) for 2 days. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate was concentrated to dryness to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (400 mg, 88%). 1H NMR (400 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.13 (d, J=5.7 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.14 (d, J=8.7 Hz, 1H), 6.58 (dd, J=5.7, 2.4 Hz, 1H), 6.32 (d, J=8.7 Hz, 1H), 5.92 (s, 2H), 2.03 (s, 3H), 1.95 (m, 1H), 0.76 (s, 4H); MS (ESI) m/z: 285.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-ed9b7898ffc1416d8c424fc11f5943a8
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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