Triethylamine → HCID 71227279, compound

HRID 713471Notes

Reaction equation

HRID 713471 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:11][N:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:27][C:28]([O:30][CH3:31])=[O:29]>C(#N)C>[CH3:31][O:30][C:28](=[O:29])[CH2:27][N:16]1[CH2:17][CH2:18][CH:13]([C:10]2[O:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:12][N:11]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 27789574-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]piperidine

Product 1

HCID 71227279HCID 71227279, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-5-(piperidin-4-yl)-1,3,4-oxadiazole (160 mg, 0.55 mmol) in acetonitrile (15 mL) was added triethylamine (0.192 mL, 1.4 mmol), then methyl 2-bromoacetate (0.066 mL, 0.715 mmol). The mixture was stirred overnight at room temperature for 8 h. The white precipitate was filtered, washed with acetonitrile, then ether. The mother liquor which contained the desired product was evaporated yielding the title compound as a white solid (100 mg) which was used without further purification. 1H NMR (400 MHz, chloroform-d) δ ppm 8.03 (dd, J=9.09, 5.05 Hz, 2H) 7.19 (t, J=8.59 Hz, 2H) 3.74 (s, 3H) 3.30 (s, 2H) 2.93-3.10 (m, 3H) 2.35-2.54 (m, 2H) 2.12 (dd, 4H). MS (m/z, MH+): 320.5

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with acetonitrile
  3. customwas evaporated

Sources & evidence

ORD record
ord-779a3c0ce0284ea9a52b044ffbc5f579
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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