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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
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HRID 520248 반응식
[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
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참가 물질

5

반응물 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

생성물 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-carboxamide수율 106.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f2691f54a909430594c34430c2b00933
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09326515B2

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