Ammonium Chloride → HCID 90410027, compound

HRID 626580Notes

Reaction equation

HRID 626580 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]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:23]([O-])=O)[N:3]=1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[NH2:23][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]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH:10]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 90410557HCID 90410557, compound

Product 1

HCID 90410027HCID 90410027, compoundYield 100.1%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.720 g, 2.097 mmol) and NH4Cl (3.37 g, 62.9 mmol) in MeOH (10 mL) and THF (10 mL) was treated with zinc dust (1.371 g, 20.97 mmol) and stirred at RT overnight. The mixture was diluted with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness to afford N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (658 mg, 100%). MS (ESI) m/z: 314.2 (M+H+).

Workup

  1. customthe solids removed via filtration
  2. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-5e3d32ac235c4253994df8cd49d8b9a9
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

Loading…