Pyridine → HCID 16722858, 화합물

HRID 2421150노트

반응식

HRID 2421150 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:26])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:37]([S:40](Cl)(=[O:42])=[O:41])([CH3:39])[CH3:38].N1C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:26][S:40]([CH:37]([CH3:39])[CH3:38])(=[O:42])=[O:41])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 824082-Propanesulfonyl chloride2회HCID 3251421Potassium bis(trimethylsilyl)amideHCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

생성물 1

HCID 16722858HCID 16722858, 화합물수율 11.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine (200 mg, 0.57 mmol) in tetrahydrofuran (5 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in tetrahydrofuran, 1.51 mL, 1.38 mmol). After stirring for 15 min at this temperature isopropylsulfonyl chloride (319 mg, 2.24 mmol) was added and stirring was continued at ambient temperature for 76 h. Further isopropylsulfonyl chloride (107 mg, 0.75 mmol) and pyridine (454 mg, 5.74) were added and stirring was continued for 24 h. The resulting suspension was extracted with ethyl acetate (20 mL) and the combined organic layers were washed with aqueous sodium carbonate (saturated). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane 50:30:20 to 20:60:20) afforded the title compound (29 mg, 11%) as a yellow solid. MS: m/e 455.2 [M+H]+.

후처리

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 24 h
  4. extractionThe resulting suspension was extracted with ethyl acetate (20 mL)
  5. washthe combined organic layers were washed with aqueous sodium carbonate (saturated)
  6. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane 50:30:20 to 20:60:20)

출처 및 근거

ORD 기록
ord-3f7d31880a784abcbd24bd966a91d701
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07956074B2

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