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

HRID 1465585ノート

反応式

HRID 1465585 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-0cfa89876a364b949a01df48851061ff
出典データセット
uspto-grants-2015_04
特許番号
US08999983B2

反応ノート

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