HCID 90409812, compound → HCID 90410556, compound

HRID 626520Notes

Reaction equation

HRID 626520 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N: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>[Ni].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]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)=[O:9])[CH:16]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 90409812HCID 90409812, compound

Product 1

HCID 90410556HCID 90410556, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 4-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide, DN-01540-085-1 (6.40 g, 17.86 mmol) and Raney Nickel (1.00 g, 17.26 mmol) in MeOH (100 mL) was hydrogenated (40 psi) in a Parr shaker flask at RT for 2 h. The catalyst from the reaction mixture was removed by filtration and washed with MeOH. The filtrate was evaporated to provide N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-4-methylpiperazine-1-carboxamide (5.80 g, 99%) as light brownish solid. MS (ESI) m/z: 329.2 (M+H+).

Workup

  1. customat RT
  2. customfor 2 h
  3. customThe catalyst from the reaction mixture was removed by filtration
  4. washwashed with MeOH
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-102b6da366d34a53a4caedc18db665c8
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

Loading…