Ammonium Chloride → HCID 90402432, compound

HRID 1049242Notes

Reaction equation

HRID 1049242 reaction equation
[CH3:1][C:2]1[S: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-]>C1COCC1.CO.[Zn]>[CH3:1][C:2]1[S: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

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 90403093HCID 90403093, compound

Product 1

HCID 90402432HCID 90402432, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 0° C. solution of 2-methyl-5-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)thiazole (0.191 g, 0.608 mmol) in THF (3 mL) and MeOH (3 mL) was treated with NH4Cl (1.3 g, 24.31 mmol) followed by the slow addition of zinc dust (0.397 g, 6.08 mmol), the mixture allowed to warm to RT and stirred for 2 h. The mixture was treated with THF, the solids removed via filtration through diatomaceous earth, washed well with THF, the filtrate treated with EtOAc, washed with 1:1 brine/satd. NaHCO3, dried over Na2SO4 and concentrated to dryness to afford 5-((2-(2-methylthiazol-5-yl)pyridin-4-yl)oxy)pyridin-2-amine (164 mg, 95%). 1H NMR (400 MHz, DMSO-d6): δ 8.34 (d, J=5.8 Hz, 1H), 8.28 (s, 1H), 7.82 (d, J=2.9 Hz, 1H), 7.50 (d, J=2.4 Hz, 1H), 7.29 (dd, J=8.9, 3.0 Hz, 1H), 6.67 (dd, J=5.8, 2.4 Hz, 1H), 6.51 (d, J=8.9 Hz, 1H), 6.03 (s, 2H), 2.64 (s, 3H); MS (ESI) m/z: 285.1 (M+H+).

Workup

  1. customthe solids removed via filtration through diatomaceous earth
  2. washwashed well with THF
  3. additionthe filtrate treated with EtOAc
  4. washwashed with 1:1 brine/satd
  5. dry with materialNaHCO3, dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-502b211318e1482b91269f56be8f09cf
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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