Triethylamine → HCID 86640042, compound

HRID 452762Notes

Reaction equation

HRID 452762 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=3)=[N:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>CN(C)C1C=CN=CC=1.O1CCCC1.C(OCC)(=O)C>[CH2:33]([O:32][C:30](=[O:31])[NH:21][C:17]1[CH:16]=[C:15]([C:13]2[O:14][C:10]([CH2:9][CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:11][N:12]=2)[CH:20]=[CH:19][N:18]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 68664139HCID 68664139, compound

Product 1

HCID 86640042HCID 86640042, compoundYield 7.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[5-[2-(3-fluorophenyl)ethyl]-1,3,4-oxadiazol-2-yl]pyridin-2-amine (280 mg, 0.985 mmol), triethylamine (0.82 mL, 5.92 mmol) and 4-dimethylaminopyridine (12 mg, 0.0985 mmol) in tetrahydrofuran (10 mL) was added benzyl chloroformate (0.70 mL, 4.92 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. 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 (30 mg, yield 7%) 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-c527b06035a24488b469947722f512b7
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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