Dimethyl Sulfoxide → HCID 71143526, 화합물

HRID 1049134노트

반응식

HRID 1049134 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[CH2:15][N:14]([C:16]2[CH:27]=[CH:26][C:19]([C:20]([NH:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH2:13]1.C(N(CC)CC)C>>[CH:23]([NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([N:14]2[CH2:13][C:12](=[O:11])[CH2:15]2)=[CH:27][CH:26]=1)([CH3:25])[CH3:24]

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 711435344-(3-Hydroxy-1-azetidinyl)-N-(1-methylethyl)benzamide

생성물 1

HCID 71143526HCID 71143526, 화합물수율 77.4%

반응 조건

온도
-78 °C

실험 절차

To a cooled (−78° C.) solution of oxalyl chloride (1.05 mL, 12.4 mmol) in dichloromethylene (20 mL) was added dropwise dimethyl sulfoxide (1.71 mL, 24.1 mmol). The mixture was stirred at −78° C. for 10 min. Then a suspension of 4-(3-hydroxyazetidin-1-yl)-N-isopropylbenzamide (1.72 g, 7.34 mmol) in dichloromethylene (20 mL) was added. The mixture was stirred at −78° C. for 1 h, and then triethylamine (7.04 mL, 50.5 mmol) was added. The mixture was stirred at −78° C. for an additional 1.5 h. The mixture was washed with aq. NaHCO3 and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The precipitates were washed with ether and collected by filtration to afford the desired product (1.32 g, 77%) which was directly used in the next step without further purification. LCMS cacld. for C13H17N2O2 (M+1)+: m/z=233.1. Found: 233.1.

후처리

  1. additionwas added
  2. stirringThe mixture was stirred at −78° C. for 1 h
  3. stirringThe mixture was stirred at −78° C. for an additional 1.5 h
  4. washThe mixture was washed with aq. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe precipitates were washed with ether
  9. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-08838eb3509b47c79edf1c364a31fda8
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382231B2

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