Diisopropylethylamine → (5S)-5-({[4-(4-fluorophenyl)piperidin-1-yl}sulfonyl]methyl)-5-methylimidazolidine-2,4-dione

HRID 32386노트

반응식

HRID 32386 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:24][C@@:25]1([CH2:32][S:33](Cl)(=[O:35])=[O:34])[C:29](=[O:30])[NH:28][C:27](=[O:31])[NH:26]1>C1COCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([S:33]([CH2:32][C@@:25]3([CH3:24])[NH:26][C:27](=[O:31])[NH:28][C:29]3=[O:30])(=[O:34])=[O:35])[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

참가 물질

5

반응물 3

HCID 81531Diisopropylethylamine2회HCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 218981684-(4-Fluoro-phenyl)-piperidine hydrochloride

생성물 1

HCID 59794371(5S)-5-({[4-(4-fluorophenyl)piperidin-1-yl}sulfonyl]methyl)-5-methylimidazolidine-2,4-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

4-(4-Fluorophenyl)piperidine hydrochloride (63 mg, 0.29 mmol) was taken up in 3 mL of dry THF, neutralized with diisopropylethylamine (50 μL, 0.29 mmol) and cooled on an ice-water bath. [(4S)-4-metyl-2,5-dioxo-imidazolodin-4-yl]methanesulfonyl chloride (80 mg, 0.35 mmol) was added and after stirring for 10 min, diisopropylethylamine (50 μL, 0.29 mmol) was added and the reaction mixture was stirred at ambient temperature until LC-MS (APCD) indicated consumption of the amine. The reaction mixture was evaporated and the residue taken up in EtOH and heated to 50° C. and allowed to cool before water was added. The precipitated product was collected and washed with EtOH/water and dried in vacuum to yield 87 mg.

후처리

  1. temperaturecooled on an ice-water bath
  2. stirringthe reaction mixture was stirred at ambient temperature until LC-MS (APCD)
  3. customconsumption of the amine
  4. customThe reaction mixture was evaporated
  5. temperatureto cool before water
  6. additionwas added
  7. customThe precipitated product was collected
  8. washwashed with EtOH/water
  9. customdried in vacuum
  10. customto yield 87 mg

출처 및 근거

ORD 기록
ord-72cdafcdd2114a89a9df74afdb6ade70
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427631B2

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