Methyl iodide → 3-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one

HRID 2206859노트

반응식

HRID 2206859 반응식
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:12]2[NH:16][C:15](=[O:17])[O:14][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC>CC#N.CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9]/[N:10]=[C:11](/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)\[C:12]2[N:16]([CH3:24])[C:15](=[O:17])[O:14][N:13]=2)[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1366263643-[(Z)-N-[(6-amino-2-pyridinyl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

생성물 1

HCID 894438773-[(E)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one수율 86.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

To a solution of 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (1 g, 3.21 mmol, 1 eq.) in MeCN (50 ml) and DMF (10 ml) was added potassium carbonate (532 mg, 3.85 mmol, 1.2 eq.) followed by iodomethane (547 mg, 3.85 mmol, 1.2 eq.). The reaction was stirred at room temperature overnight. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(6-aminopyridin-2-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (906 mg, 85% yield) has a white solid.

후처리

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with EtOAc (3×50 ml)
  3. washwashed with aq. sat. NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-c3e29ded53464c6984d9ff8c7e414d39
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09375010B2

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