Potassium Carbonate → HCID 68664101, compound

HRID 452766Notes

Reaction equation

HRID 452766 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=2)=[N:9][N:8]=1.ClC(OCC(Cl)(Cl)Cl)=O.[C:31](=[O:34])([O-])[O-].[K+].[K+].[NH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:31]([NH:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[O:34])[CH:13]=2)=[N:9][N:8]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 68664402HCID 68664402, compound

Product 1

HCID 68664101HCID 68664101, compoundYield 57%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-[5-[(3-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]pyridin-2-amine (408 mg, 1.35 mmol) and triethylamine (0.468 mL) in tetrahydrofuran (20 mL) was added 2,2,2-trichloroethyl chloroformate (0.558 mL, 4.05 mmol) under ice-cooling, and the resulting mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10), and the obtained compound was dissolved in N,N-dimethylformamide (15 mL). To this solution were added potassium carbonate (383 mg, 2.77 mmol), water (3 mL) and 2-(aminomethyl)pyridine (300 mg, 2.77 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 30 min and at 50° C. for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10, ethyl acetate/methanol=9/1), and recrystallized from diethyl ether/methanol to give the title compound (313 mg, yield 57%) as colorless crystals.

Workup

  1. temperaturecooling
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10)
  6. dissolutionthe obtained compound was dissolved in N,N-dimethylformamide (15 mL)
  7. temperaturecooling
  8. stirringthe resulting mixture was stirred at room temperature for 30 min and at 50° C. for 30 min
  9. washwashed with water and saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/10, ethyl acetate/methanol=9/1)
  13. customrecrystallized from diethyl ether/methanol

Sources & evidence

ORD record
ord-10a550e659c441f18e47b1aa06e28e6c
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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