Ammonium Chloride → HCID 90409862, compound

HRID 626578Notes

Reaction equation

HRID 626578 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[C:19]([CH3:27])=[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]=[C:19]([CH3:27])[C:18]([O:17][C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:8]([N: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

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 90409400HCID 90409400, compound

Product 1

HCID 90409862HCID 90409862, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-methyl-N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperazine-1-carboxamide (0.400 g, 1.074 mmol) in MeOH (20 mL) was treated with NH4Cl (2.00 g, 37.4 mmol) followed by zinc powder (1.00 g, 15.29 mmol) and the mixture 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-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)-4-methylpiperazine-1-carboxamide (290 mg, 79%). MS (ESI) m/z: 343.2 (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-b5d05994eda3438b96617cb673a262b7
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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