Triethylamine → HCID 68663046, compound

HRID 452760Notes

Reaction equation

HRID 452760 reaction equation
FC1C=C(C=CC=1)CSC1OC(C2C=CN=C(N)C=2)=NN=1.C(N(CC)CC)C.C(Cl)(=O)C=C.[C:34]([N:38]([C:43]1[CH:48]=[C:47]([C:49]2[O:50][C:51]([S:54][CH2:55][C:56]3[CH:61]=[CH:60][CH:59]=[C:58]([F:62])[CH:57]=3)=[N:52][N:53]=2)[CH:46]=[CH:45][N:44]=1)C(=O)C=C)(=[O:37])[CH:35]=[CH2:36]>O1CCCC1.C(OCC)(=O)C>[F:62][C:58]1[CH:57]=[C:56]([CH:61]=[CH:60][CH:59]=1)[CH2:55][S:54][C:51]1[O:50][C:49]([C:47]2[CH:46]=[CH:45][N:44]=[C:43]([NH:38][C:34](=[O:37])[CH:35]=[CH2:36])[CH:48]=2)=[N:53][N:52]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 68663387HCID 68663387, compoundHCID 68664402HCID 68664402, compound

Product 1

HCID 68663046HCID 68663046, compoundYield 61%

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 (1.35 g, 4.75 mmol) and triethylamine (1.98 mL, 14.25 mmol) in tetrahydrofuran (100 mL) was added acryloyl chloride (0.97 mL, 11.88 mmol) at 0° C., 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=95/5-0/100) to give a mixture (1/1, 1.08 g, yield 61%) of N-[4-[5-[(3-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]-2-pyridyl]acrylamide and N-acryloyl-N-[4-[5-[(3-fluorobenzyl)thio]-1,3,4-oxadiazol-2-yl]-2-pyridyl]acrylamide as pale-yellow 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 silica gel column chromatography (hexane/ethyl acetate=95/5-0/100)

Sources & evidence

ORD record
ord-0dd108bb7f504a05828c5e1e5eff386c
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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