Ammonium Chloride → HCID 90402691, compound

HRID 1049259Notes

Reaction equation

HRID 1049259 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:6]([CH3:21])[CH:5]=[C:4]([N+:22]([O-])=O)[N:3]=1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[CH3:21][C:6]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([C:15]3[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=3)[CH:10]=2)=[C:2]([CH3:1])[N:3]=[C:4]([NH2:22])[CH:5]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 90402579HCID 90402579, compound

Product 1

HCID 90402691HCID 90402691, compoundYield 60.3%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. mixture of 2,4-dimethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (285 mg, 0.876 mmol) and NH4Cl (1.87 g, 35 mmol) in MeOH (5 mL) and THF (5 mL) was treated portion-wise with zinc dust (573 mg, 8.76 mmol), allowed to warm to RT and stirred overnight. The mixture was diluted with EtOAc, warmed slightly, the solids removed via filtration through diatomaceous earth and washed with EtOAc. The filtrate was concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine (156 mg, 60%) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 8.30 (d, J=5.7 Hz, 1H), 8.23 (s, 1H), 7.93 (s, 1H), 7.10 (d, J=2.4 Hz, 1H), 6.44 (dd, J=5.7, 2.4 Hz, 1H), 6.22 (s, 1H), 5.81 (s, 2H), 3.84 (s, 3H), 2.02 (s, 3H), 1.92 (s, 3H); MS (ESI) m/z: 296.1 (M+H+).

Workup

  1. temperaturewarmed slightly
  2. customthe solids removed via filtration through diatomaceous earth
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated to dryness
  5. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-2d34f75a4efe491fbd0f54b40803c348
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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