Pyridine → Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylate

HRID 1820305노트

반응식

HRID 1820305 반응식
O[CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([C:13]([O:15][CH3:16])=[O:14])([CH2:6]3)[CH2:4]1)[CH2:10]2.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[N:43][CH:44]=1>C(Cl)Cl.O>[CH3:38][C:39]1[CH:40]=[CH:41][C:42]([NH:45][CH:46]2[CH2:51][CH2:50][N:49]([CH2:10][C:9]34[CH2:2][CH:3]5[CH2:12][CH:7]([CH2:6][C:5]([C:13]([O:15][CH3:16])=[O:14])([CH2:4]5)[CH2:11]3)[CH2:8]4)[CH2:48][CH2:47]2)=[N:43][CH:44]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 18410517Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylateHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amine

생성물 1

HCID 23109891Methyl 3-[4-(5-methylpyridin-2-yl)aminopiperidin-1-ylmethyl]tricyclo[3.3.1.13,7]decane--1-carboxylate수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

After dissolving methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate (0.1648 g, 0.735 mmol) and pyridine (0.0829 g, 1.05 mmol) in methylene chloride (5 mL), trifluoromethanesulfonic anhydride (0.185 mL, 1.11 mmol) was added dropwise while cooling on ice and the mixture was stirred for 1 hour. Water (10 mL) was added to the reaction mixture, and after extraction with ethyl acetate (20 mL), the extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order and dried over anhydrous magnesium sulfate, and then 4-(5-methylpyridin-2-yl)aminopiperidine (0.2995 g, 1.57 mmol) was mixed therewith and the solvent was distilled off under reduced pressure. The obtained yellow oil was heated at 60° C. for 1 hour. It was then subjected to chromatography (50 g Merck Art. 9385, methylene chloride:methanol:ammonia water=97:3:0.2) to obtain the title compound as a white solid (0.2398 g, 0.603 mmole) (82% yield).

후처리

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. extractionafter extraction with ethyl acetate (20 mL)
  4. washthe extract was washed with 1N HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (10 mL) in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-f040a2d2832f4304ab912427de10da89
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601843B2

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