Triethylamine → HCID 68663959, compound

HRID 452756Notes

Reaction equation

HRID 452756 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.C(N(CC)CC)C.[C:29]1([CH2:35][CH2:36][C:37](Cl)=[O:38])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1.C(OCC)(=O)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:37](=[O:38])[CH2:36][CH2:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:13]=2)=[N:9][N:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 68664402HCID 68664402, compound

Product 1

HCID 68663959HCID 68663959, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-[(3-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]pyridin-2-amine (360 mg, 1.19 mmol) and triethylamine (290 mg, 2.86 mmol) in tetrahydrofuran (30 mL) was added 3-phenylpropionyl chloride (482 mg, 2.86 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 15 hr. 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 basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100) and recrystallized from hexane/ethyl acetate to give the title compound (205 mg, yield 40%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ede6510a3dc84eb5b4f6664d5b7846b1
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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