Ammonium Chloride → HCID 90410556, compound

HRID 626519Notes

Reaction equation

HRID 626519 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.[NH4+].[Cl-]>CO.[Zn]>[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

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90409812HCID 90409812, compound

Product 1

HCID 90410556HCID 90410556, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (0.400 g, 1.116 mmol) in MeOH (20 mL) was treated with NH4Cl (2.00 g, 37.4 mmol) and zinc powder (1.00 g, 15.29 mmol) and stirred at RT overnight. The solids were removed via filtration, washed with DCM and the filtrate concentrated to dryness. The residue was treated with DCM and a few drops of MeOH, the solids again removed via filtration and the filtrate concentrated to dryness to afford N-(4-((6-aminopyridin-3-yl)oxy)pyridin-2-yl)-4-methylpiperazine-1-carboxamide (346 mg, 94%). MS (ESI) m/z: 329.2 (M+H+).

Workup

  1. customThe solids were removed via filtration
  2. washwashed with DCM
  3. concentrationthe filtrate concentrated to dryness
  4. additionThe residue was treated with DCM and a few drops of MeOH
  5. customthe solids again removed via filtration
  6. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-f7771af82bf14309af1188182a76dd3e
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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