Ammonium Chloride → HCID 90403597, compound

HRID 2278923Notes

Reaction equation

HRID 2278923 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[N:16][C:17]([N+:20]([O-])=O)=[CH:18][CH:19]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1.[NH4+].[Cl-]>CO.C1COCC1.CCOC(C)=O.[Zn]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[N:16][CH:15]=3)[CH:10]=[CH:9][N:8]=2)=[CH:5][N:6]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 90403371HCID 90403371, compound

Product 1

HCID 90403597HCID 90403597, compoundYield 112%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. mixture of 2-methyl-5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)oxazole (323 mg, 1.083 mmol) and NH4Cl (2.317 g, 43.3 mmol) in MeOH (8 mL) and THF (8 mL) was treated portion-wise with zinc dust (708 mg, 10.83 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, treated with EtOAc, heated to reflux, the solids removed via hot filtration and the filtrate concentrated to dryness to afford 5-((2-(2-methyloxazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (324 mg, 112%). 1H NMR (400 MHz, DMSO-d6): δ 8.43 (d, J=5.7 Hz, 1 H), 7.83 (d, J=2.9 Hz, 1 H), 7.60 (s, 1 H), 7.31 (dd, J=8.9, 3.0 Hz, 1 H), 7.06 (d, J=2.5 Hz, 1 H), 6.83 (dd, J=5.7, 2.5 Hz, 1 H), 6.53 (d, J=8.9 Hz, 1 H), 6.07 (s, 2 H), 2.46 (s, 3 H); MS (ESI) m/z: 269.1 (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. additiontreated with EtOAc
  6. temperatureheated
  7. temperatureto reflux
  8. customthe solids removed via hot filtration
  9. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-b2dd72f70e8f4dadab77c1e325e7936c
Source dataset
uspto-grants-2015_09
Patent number
US09133183B2

Reaction notes

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