Ammonium Chloride → HCID 90403023, compound

HRID 1049374Notes

Reaction equation

HRID 1049374 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[S:19][CH:18]=[N:17][CH:16]=3)[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:20]([O-])=O)[N:3]=1.[NH4+].[Cl-]>C1COCC1.CO.[Zn]>[CH3:1][C:2]1[N:3]=[C:4]([NH2:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]2[S:19][CH:18]=[N:17][CH:16]=2)[CH:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90404051HCID 90404051, compound

Product 1

HCID 90403023HCID 90403023, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (0.34 g, 1.082 mmol) in THF (10 mL) and MeOH (10 mL) was treated with NH4Cl (2.314 g, 43.3 mmol) followed by zinc powder (1.061 g, 16.23 mmol) and stirred at RT for 24 h. The solids were removed via filtration through diatomaceous earth, washed well with MeOH and the filtrate concentrated to dryness. The residue was treated with water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was suspended in 30% EtOAc/Hex, sonicated and the solid collected via filtration and dried to afford 6-methyl-5-((2-(thiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (220 mg, 72%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.58 (s, 1H), 8.37 (d, J=5.8 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.20 (d, J=8.7 Hz, 1H), 6.61 (dd, J=5.8, 2.4 Hz, 1H), 6.35 (d, J=8.7 Hz, 1H), 5.97 (s, 2H), 2.08 (s, 3H); MS (ESI) m/z: 285.1 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed well with MeOH
  3. concentrationthe filtrate concentrated to dryness
  4. additionThe residue was treated with water
  5. extractionextracted with EtOAc (3×)
  6. washthe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness
  9. customsonicated
  10. filtrationthe solid collected via filtration
  11. customdried

Sources & evidence

ORD record
ord-837618ed5cac4ee189698d9711a66438
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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