HCID 23144680, compound → 2-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole

HRID 2076918Notes

Reaction equation

HRID 2076918 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19]C(=O)OC(C)(C)C)[S:9][C:10]=1[C:11]([CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12]>FC(F)(F)C(O)=O>[NH2:19][C:8]1[S:9][C:10]([C:11]([CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[O:12])=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:7]=1

Participants

3

Reactant 1

HCID 23144680HCID 23144680, compound

Product 1

HCID 866124682-Amino-4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazoleYield 81.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazole-2-yl]carbamate (350 mg, 0.93 mmol) obtained in Step 2 was dissolved in trifluoroacetic acid (5 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and saturated sodium bicarbonate aqueous solution were added thereto, then the mixture was extracted. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4) to give a title compound (212 mg, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate and saturated sodium bicarbonate aqueous solution
  2. additionwere added
  3. extractionthe mixture was extracted
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-351d8e21dde14c1f9cee2aec2d1e3295
Source dataset
uspto-grants-2011_04
Patent number
US07928098B2

Reaction notes

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