Pyridine → N-[4-[[(Z)-[(2-methyl-5-oxo-1,2,4-oxadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-1,3-thiazol-2-yl]-2,3-dihydro-1,4-benzodioxine-3-carboxamide

HRID 520248

Reaction equation

HRID 520248 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.[O:30]1[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2[O:33][CH2:32][CH:31]1[C:40](Cl)=[O:41]>ClCCl>[CH3:17][N:12]1[C:11](/[C:10](=[N:9]\[O:8][CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:40]([CH:31]3[O:30][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=4[O:33][CH2:32]3)=[O:41])[S:3][CH:4]=2)/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:15][C:14](=[O:16])[O:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27354472,3-Dihydro-1,4-benzodioxin-2-carbonyl 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 71627019N-[4-[[(Z)-[(2-methyl-5-oxo-1,2,4-oxadiazol-3-yl)-phenylmethylidene]amino]oxymethyl]-1,3-thiazol-2-yl]-2,3-dihydro-1,4-benzodioxine-3-carboxamideYield 106.4%

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 (120 mg, 0.362 mmol, 1 eq.) and pyridine (0.044 ml, 0.543 mmol, 1.5 eq) in dry dichloromethane (2.0 ml) at room temperature was added 2,3-dihydro-1,4-benzodioxine-2-carbonyl chloride (108 mg, 0.543 mmol, 1.5 eq) and stirring was allowed overnight. The reaction was quenched by addition of water and concentrated to dryness. The residue was taken in EtOAc and 0.5 ml of 1N NaOH was added. The solution was filtered through a chemelut pad and washed with EtOAc. After concentration, the residue was purified by chromatography on silica gel to give 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}-2,3-dihydro-1,4-benzodioxine-2-carboxamide (190 mg, 99% yield).

Workup

  1. customThe reaction was quenched by addition of water
  2. concentrationconcentrated to dryness
  3. addition0.5 ml of 1N NaOH was added
  4. filtrationThe solution was filtered through a chemelut pad
  5. washwashed with EtOAc
  6. concentrationAfter concentration
  7. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f2691f54a909430594c34430c2b00933
Source dataset
uspto-grants-2016_05
Patent number
US09326515B2

Linked notes

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