Trimethylsilyl iodide → N-(6-(3-chloro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

HRID 870002ノート

反応式

HRID 870002 の反応式
[Cl:1][C:2]1[C:3]([O:32]C)=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([NH:15][C:16]([C:18]2([C:21]3[CH:31]=[CH:30][C:24]4[O:25][C:26]([F:29])([F:28])[O:27][C:23]=4[CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[N:9]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:3](=[O:32])[NH:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[C:10]([NH:15][C:16]([C:18]2([C:21]3[CH:31]=[CH:30][C:24]4[O:25][C:26]([F:28])([F:29])[O:27][C:23]=4[CH:22]=3)[CH2:20][CH2:19]2)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14]

参加物

4

反応物 2

HCID 85247Trimethylsilyl iodideHCID 91096555N-(3'-chloro-2'-methoxy-3-methyl-2,4'-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

生成物 1

HCID 117640728N-(6-(3-chloro-2-oxo-1,2-dihydropyridin-4-yl)-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To N-(3′-chloro-2′-methoxy-3-methyl-2,4′-bipyridin-6-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (71 mg, 0.15 mmol) in chloroform (2 mL) was added iodotrimethylsilane (90 mg, 0.45 mmol). The reaction mixture was stirred at room temperature for six hours. The reaction mixture was evaporated to dryness and purified by reverse phase preparative liquid chromatography to yield the product as a trifluoroacetic acid salt. The salt was dissolved in dichloromethane (5 mL) and washed with a saturated sodium bicarbonate solution (2×5 mL). The organics were dried over sodium sulfate and evaporated to yield the product (23 mg, 33%). ESI-MS m/z calc. 459.08. found 460.3 (M+1)+. Retention time 1.11 minutes. 1H NMR (400 MHz, DMSO-d6) δ 12.26 (s, 1H), 9.11 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 7.55 (m, 1H), 7.44 (d, J=6.6 Hz, 1H), 7.40-7.38 (m, 1H), 7.35-7.32 (m, 1H), 6.11 (d, J=6.6 Hz, 1H), 2.06 (s, 3H), 1.51-1.50 (m, 2H), 1.17-1.15 (m, 2H).

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. custompurified by reverse phase preparative liquid chromatography

出典と根拠

ORDレコード
ord-21bd8aaf4f6643d485c38150ec44eeaf
出典データセット
uspto-grants-2015_03
特許番号
US08969386B2

反応ノート

読み込み中…