5-(Chloromethyl)-2-(trifluoromethyl)pyridine → 5-(4-methoxyphenyl)-1-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyridin-2(1H)-one hydrochloride

HRID 1948200

반응식

HRID 1948200 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[Cl:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:26])[F:25])=[N:22][CH:23]=1>>[ClH:16].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:15])[N:13]([CH2:17][C:18]3[CH:23]=[N:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=3)[CH:14]=2)=[CH:5][CH:4]=1

참가 물질

3

반응물 2

HCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridineHCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-one

생성물 1

HCID 693448115-(4-methoxyphenyl)-1-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyridin-2(1H)-one hydrochloride수율 17%

실험 절차

According to Scheme 5 Step 2: The title compound was prepared from 5-(4-methoxyphenyl)-(1H)-pyridin-2-one (1 eq, 0.50 mmol, 0.10 g, Example 7 Step 1) and 5-(chloromethyl)-2-(trifluoromethyl)pyridine (1.5 eq, 0.74 mmol, 0.15 g) according to the procedure described for Example 1 Step 2. Reaction conditions: 6 hours at 70° C. and 48 hours at room temperature. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2, CH2Cl2/AcOEt 90/10). The purified oil was dissolved in Et2O and HCl (4M in dioxane) was added. The resulting precipitate was filtered, dried to afford 5-(4-methoxyphenyl)-1-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyridin-2(1H)-one hydrochloride (83 μmol, 30 mg, 17%) as a white solid.

후처리

  1. customReaction conditions
  2. custom6 hours
  3. customat 70° C.
  4. custom48 hours
  5. customat room temperature
  6. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 10 g SiO2, CH2Cl2/AcOEt 90/10)
  7. dissolutionThe purified oil was dissolved in Et2O
  8. additionHCl (4M in dioxane) was added
  9. filtrationThe resulting precipitate was filtered
  10. customdried

출처 및 근거

ORD 기록
ord-3624782ec97743f8b869338ce8e49d32
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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