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

HRID 1820303ノート

反応式

HRID 1820303 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-106ed0c2fb404c9f8f1005b694abcf23
出典データセット
uspto-grants-2009_10
特許番号
US07601843B2

反応ノート

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