Pyridine → HCID 71627020, compound

HRID 520249Notes

Reaction equation

HRID 520249 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.N1C=CC=CC=1.[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](Cl)=[O:39])=[CH:33][CH:32]=1>ClCCl>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38]([NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](\[C:11]3[N:12]([CH3:17])[O:13][C:14](=[O:16])[N:15]=3)/[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:6]=2)=[O:39])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 906924-Chlorophenylacetyl chlorideHCID 716269453-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-2-methyl-1,2,4-oxadiazol-5-one

Product 1

HCID 71627020HCID 71627020, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (300 mg, 0.905 mmol, 1 eq.) and pyridine (0.110 ml, 1.36 mmol, 1.5 eq) in dry dichloromethane (4.0 ml) at room temperature was added 4-chlorophenyl acetyl chloride (0.20 mL, 1.36 mmol, 1.5 eq) and stirring was allowed for 2 h. The reaction was quenched by addition of 2 ml of 1N NaOH. The layers were separated and the organic layer was dried over MgSO4. After concentration, the residue was purified by chromatography on silica gel to give 2-(4-chlorophenyl)-N-{4-[({[(Z)-(2-methyl-5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)(phenyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-yl}acetamide (365 mg, 79% yield).

Workup

  1. customThe reaction was quenched by addition of 2 ml of 1N NaOH
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationAfter concentration
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a02f4e523ab4e71858c08088c74ea19
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Reaction notes

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