Triethylamine → N-[1-(3-tert-Butyldimethylsiloxy-3-cyclohexylpropyl)piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide

HRID 1820303노트

반응식

HRID 1820303 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[O:9]([CH:17]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=2)[CH2:22][CH2:21]1)[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)Cl>[O:9]([CH:17]([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([N:26]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=2)[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[CH2:22][CH2:21]1)[Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:11])[CH3:12]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 231099081-(3-Tert-butyldimethylsiloxy-3-cyclohexylpropyl)-4-(5-methylpyridin-2-yl)aminopiperidine

생성물 1

HCID 23109895N-[1-(3-tert-Butyldimethylsiloxy-3-cyclohexylpropyl)piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide수율 89.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

After adding 2-furoyl chloride (0.14 mL, 1.4 mmol) dropwise to a solution of 1-(3-tert-butyldimethylsiloxy-3-cyclohexylpropyl)-4-(5-methylpyridin-2-yl)aminopiperidine (423 mg, 0.95 mmol) and triethylamine (0.264 mL) in methylene chloride (4 mL) while cooling on ice, the mixture was stirred at room temperature for 18 hours. NH silica Chromatorex DM1020 was added to the reaction mixture, which was then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1) to obtain the title compound as an oil (458 mg) (89.4% yield).

후처리

  1. temperaturewhile cooling on ice
  2. additionNH silica Chromatorex DM1020 was added to the reaction mixture, which
  3. concentrationwas then concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (60 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-106ed0c2fb404c9f8f1005b694abcf23
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601843B2

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