Pyridine → HCID 71627023, compound

HRID 520252Notes

Reaction equation

HRID 520252 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:11]2[N:12]([CH3:17])[O:13][C:14](=[O:16])[N:15]=2)[N:6]=1.FC1C=CC([ClH][C:32](=[O:34])[O-:33])=CC=1.N1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH:41]1([OH:47])CCCCC1.[C:48](#N)C>>[CH3:41][O:47][C:20]1[CH:19]=[C:18](/[C:10](=[N:9]/[O:8][CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:32](=[O:34])[O:33][CH:36]3[CH2:48][CH2:40][CH2:39][CH2:38][CH2:37]3)[S:3][CH:4]=2)/[C:11]2[N:12]([CH3:17])[O:13][C:14](=[O:16])[N:15]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 7966CyclohexanolHCID 716269453-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-2-methyl-1,2,4-oxadiazol-5-one

Product 1

HCID 71627023HCID 71627023, compoundYield 77%

Procedure

To a solution of 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-2-methyl-1,2,4-oxadiazol-5(2H)-one (100 mg, 0.277 mmol, 1 eq.) in acetonitrile (2 ml) was added 4-fluorophenylcarbonochloridate (0.040 mL, 0.304 mmol, 1.1 eq.), followed by pyridine (0.022 mL, 0.277 mmol, 1 eq.) and stirring was allowed for 2 hours at room temperature. Cyclohexanol (0.032 mL, 0.304 mmol, 1.1 eq.) was then added and the resulting mixture was refluxed for 15 h. After concentration, the residue was purified by chromatography on silica gel to give Cyclohexyl {4-[({[(Z)-(3-methoxyphenyl)(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}carbamate (110 mg, 77% yield) as a white solid.

Workup

  1. temperaturethe resulting mixture was refluxed for 15 h
  2. concentrationAfter concentration
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e0eee15586c04438aab6348bacf0f8ff
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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