Hydrogen Peroxide → N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

HRID 1465585노트

반응식

HRID 1465585 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([S:12][C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]3[N:21]=[C:22]([NH:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[S:23][CH:24]=3)=[C:15]([CH3:34])[CH:14]=2)=[N:10][CH:11]=1.C(OC(=O)C)(=[O:37])C.OO>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([S:12]([C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]3[N:21]=[C:22]([NH:25][C:26](=[O:33])[C:27]4[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=4)[S:23][CH:24]=3)=[C:15]([CH3:34])[CH:14]=2)=[O:37])=[N:10][CH:11]=1

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 71566783N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

생성물 1

HCID 86690888N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide수율 49%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 27 (200.0 mg, 0.41 mmol, 1.0 equiv), acetic anhydride (0.040 mL, 0.45 mmol, 1.1 equiv), 30% hydrogen peroxide (201.1 mg, 5.94 mmol, 4.4 equiv), and silica gel (81.1 mg, 230-400 mesh) in dichloromethane (5.0 mL) was stirred at room temperature for 16 h. The solution was concentrated under reduced pressure, and the residue was re-dissolved in EtOAc (30 mL). The solution was washed with saturated aqueous NaHCO3 (20 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (90% EtOAc in hexanes as eluant) to provide to provide N-(4-{4-(5-(2-methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (32, 100.3 mg, 0.2 mmol) as yellow solids in 49% yield: 1H NMR (DMSO-d6, 500 MHz) δ 13.05 (s, 1 H), 8.81 (d, J=5.5 Hz, 2 H), 8.68 (s, 1 H), 8.40 (s, 1 H), 7.98 (d, J=5.5 Hz, 2 H), 7.50 (s, 2 H), 7.26 (s, 1 H), 4.47-4.48 (m, 2 H), 3.67-3.69 (m, 2 H), 3.29 (s, 3 H), 2.14 (s, 6 H); ESI-MS: m/z 510.1 (M+H)+.

후처리

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue was re-dissolved in EtOAc (30 mL)
  3. washThe solution was washed with saturated aqueous NaHCO3 (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (90% EtOAc in hexanes as eluant)
  7. customto provide

출처 및 근거

ORD 기록
ord-0cfa89876a364b949a01df48851061ff
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

반응 노트

불러오는 중…