Triethylamine → N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

HRID 2223913노트

반응식

HRID 2223913 반응식
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][C:15]2([CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH:26]([NH:29][C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:9]=[C:8]([CH2:37][O:38][C:39](=[O:41])[CH3:40])[CH:7]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[O:49]1[CH:53]=[CH:52][CH:51]=[C:50]1[C:54](Cl)=[O:55]>ClCCl>[C:39]([O:38][CH2:37][C:8]1[CH:9]=[C:10]([CH:11]=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH:7]=1)[O:12][CH2:13][CH2:14][C:15]1([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([N:29]([C:30]3[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=3)[C:54]([C:50]3[O:49][CH:53]=[CH:52][CH:51]=3)=[O:55])[CH2:25][CH2:24]2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)(=[O:41])[CH3:40]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 597148451,3-Diacetoxymethyl-5-[2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzene

생성물 1

HCID 69144599N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1,3-diacetoxymethyl-5-[2-[1-[2-[4-(p-toluidino)piperidin-1-yl]ethyl]cyclohexyl]ethoxy]benzene (synthesized in Example 33) (222 mg) dissolved in dichloromethane (4 mL) was added triethylamine (0.11 mL). 2-Furoyl chloride (0.06 mL) was added to the solution under ice cooling. The temperature was allowed to rise to room temperature, and the solution was stirred for 1 hour. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)] to give N-[1-[2-[1-[2-[3,5-bis(acetoxymethyl)phenoxy]ethyl]cyclohexyl]ethyl]piperidin-4-yl]-N-(p-tolyl)-2-furancarboxamide (276 mg). This product was subjected to the subsequent step without further purification.

후처리

  1. customto rise to room temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography [silica gel, chloroform-methanol (10:1)]

출처 및 근거

ORD 기록
ord-5609a96e6b9b4fe6b18983f29a007461
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375115B2

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