Hydrochloric Acid → 2-Pyridin-2-yl-thiazol-5-ylamine

HRID 1260324Notes

Reaction equation

HRID 1260324 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:10][CH:9]=1)(C)(C)C.Cl>O1CCOCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]1[S:12][C:8]([NH2:7])=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67299899(2-Pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester

Product 1

HCID 457887092-Pyridin-2-yl-thiazol-5-ylamineYield 61.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (2-pyridin-2-yl-thiazol-5-yl)-carbamic acid tert-butyl ester (200 mg, 0.72 mmol) in dioxane (3 ml) was treated with 4M HCl in dioxane (3 ml) and the resulting suspension was stirred at ambient temperature overnight. The reaction mixture was filtrated and the precipitate was dissolved in sodium hydroxide (20 ml, 0.5M aqueous solution) and extracted with dichloromethane. The combined organic phases were dried and the solvent was evaporated to yield the product as orange solid (78 mg, 60%) which was used without any further purification. MS: M=178.1 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtrated
  2. dissolutionthe precipitate was dissolved in sodium hydroxide (20 ml, 0.5M aqueous solution)
  3. extractionextracted with dichloromethane
  4. customThe combined organic phases were dried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-541a556610bf41adbb89e0bba3fa2393
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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