Hydrazine hydrate (1:1) → N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

HRID 626505Notes

Reaction equation

HRID 626505 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([CH:20]3[CH2:21][CH2:22]3)=[O:19])[CH:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90410505N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 90409531N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamideYield 87%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.50 g, 5.00 mmol) in MeOH (30 mL) was treated with hydrazine hydrate (1.50 g, 30.0 mmol) followed by Raney nickel (0.300 g, 5.11 mmol) and stirred at RT for 3 h. The solids were removed via filtration through diatomaceous earth, rinsed with DCM, then MeOH and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (1.17 g, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.21 (s, 1H), 8.56 (d, J=5.7 Hz, 1H), 8.19 (s, 1H), 8.01 (s, 1H), 7.68 (d, J=8.9 Hz, 1H), 7.06 (m, 1H), 6.92 (d, J=8.9 Hz, 1H), 6.43 (s, 2H), 2.37 (m, 1H), 1.18 (s, 4H); MS (ESI) m/z: 271.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washrinsed with DCM
  3. concentrationMeOH and the filtrate concentrated to dryness

Sources & evidence

ORD record
ord-f0cbb2f269bd473abfe4debeb25ea922
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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