Triethylamine → HCID 57749236, compound

HRID 1874517Notes

Reaction equation

HRID 1874517 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17]C)=[O:16])[N:5]=2.C(N(CC)CC)C.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1>O1CCCC1.O>[CH:29]1([C:32]([NH:1][C:2]2[S:3][C:4]3[C:9]([N:10]=2)=[CH:8][CH:7]=[C:6]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([OH:17])=[O:16])[N:5]=3)=[O:33])[CH2:31][CH2:30]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 57749262HCID 57749262, compound

Product 1

HCID 57749236HCID 57749236, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]benzoate (4.20 g, 13.9 mmol) and triethylamine (3.47 μL, 25.1 mmol) in tetrahydrofuran (40 mL) was added with stirring under ice-cooling cyclopropanecarbonyl chloride (1.52 mL, 16.7 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was dissolved in ethanol (50 mL). 8N Aqueous sodium hydroxide solution (7 mL) was added thereto, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was adjusted to pH 4 with 6N hydrochloric acid, and the precipitated solid was collected by filtration and washed with water to give the title compound (3.90 g, 79%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltrated
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in ethanol (50 mL)
  8. addition8N Aqueous sodium hydroxide solution (7 mL) was added
  9. stirringthe mixture was stirred at room temperature for 3 hr
  10. filtrationthe precipitated solid was collected by filtration
  11. washwashed with water

Sources & evidence

ORD record
ord-0a3030d778684fa18112cd51b29c135f
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…