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Ethyl isocyanate → N-ethyl-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-1-piperidinecarboxamide

HRID 748807
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HRID 748807 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34].C(=O)(O)[O-].[Na+]>ClCCl.C(OC(C)C)(C)C>[CH2:33]([NH:35][C:36]([N:15]1[CH2:16][CH2:17][C:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)(=[O:10])=[O:11])([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:13][CH2:14]1)=[O:37])[CH3:34]
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참가 물질

7

반응물 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 692029464-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine Hydrochloride

생성물 1

HCID 59750838N-ethyl-4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-1-piperidinecarboxamide수율 85%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 7914Diisopropyl Ether용매

실험 절차

The 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)piperidine hydrochloride (80 mg, 0.20 mmol) obtained in Example 260 and triethylamine (0.092 ml, 0.66 mmol) were dissolved in dichloromethane (4 ml), followed by the addition of ethyl isocyanate (0.027 ml, 0.34 mmol) at room temperature. After stirring at room temperature for 6 hours, a saturated aqueous solution of sodium bicarbonate (0.5 ml) was added. The residue obtained by concentrating the reaction mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the dichloromethane:methanol=50:1 eluate was concentrated under reduced pressure to give a white solid. The resulting solid was washed with diisopropyl ether, whereby the title compound (74 mg, 0.17 mmol, 85%) was obtained as a white powder.

후처리

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customthe fraction obtained from the dichloromethane
  4. concentrationmethanol=50:1 eluate was concentrated under reduced pressure
  5. customto give a white solid

출처 및 근거

ORD 기록
ord-59ebad614a6a47d58501e596b634a73a
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07399775B2

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