2,4,6-Trifluorobenzoyl chloride → Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)

HRID 404228

반응식

HRID 404228 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1.[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:19]=1[C:20]([Cl:22])=[O:21]>O1CCOCC1>[ClH:22].[F:17][C:18]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[O:9])[N:3]=1)=[O:21]

참가 물질

4

반응물 2

HCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 11401723(6-Aminopyridin-2-yl)(1-methylpiperidin-4-yl)methanone

생성물 1

HCID 17980336Benzamide, 2,4,6-trifluoro-N-(6-((1-methyl-4-piperidinyl)carbonyl)-2-pyridinyl)-, hydrochloride (1:1)수율 100%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Combine 2-amino-6-(1-methylpiperidin-4-ylcarbonyl)pyridine (0.20 g, 0.92 mmol), 2,4,6-Trifluorobenzoyl chloride (0.357 g, 1.84 mmol), and 1,4-Dioxane (10 mL), and stir while heating at reflux. After 3 hr., cool the reaction mixture to ambient temperature and concentrate. Load the concentrated mixture onto an SCX column (10 g), wash with methanol, and elute with 2M ammonia in methanol. Concentrate the eluent to obtain the free base of the title compound as an oil (0.365 g (>100%)). Dissolve the oil in methanol (5 mL) and treat with ammonium chloride (0.05 g, 0.92 mmol). Concentrate the mixture and dry under vacuum to obtain the title compound. HRMS Obs. m/z 378.1435, Calc. m/z 378.1429; m.p. 255° C. (dec).

후처리

  1. temperaturewhile heating
  2. temperatureat reflux
  3. concentrationconcentrate
  4. washLoad the concentrated mixture onto an SCX column (10 g), wash with methanol
  5. washelute with 2M ammonia in methanol
  6. concentrationConcentrate the eluent

출처 및 근거

ORD 기록
ord-2a6312686e8842c5881fe80d6a74becd
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748459B2

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