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 870002노트

반응식

HRID 870002 반응식
[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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-21bd8aaf4f6643d485c38150ec44eeaf
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969386B2

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