Cesium carbonate → 1-(2-isopropylphenyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)urea

HRID 62072

반응식

HRID 62072 반응식
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[N-:28]=[C:29]=[O:30].[F:31][C:32]([F:56])([F:55])[O:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH:44]=[N:43][C:42]([C:45]3[CH:50]=[CH:49][C:48]([CH2:51][CH2:52][CH2:53]N)=[CH:47][CH:46]=3)=[N:41]2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.O.C(#N)C>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:29]([NH:28][CH2:53][CH2:52][CH2:51][C:48]1[CH:47]=[CH:46][C:45]([C:42]2[N:43]=[CH:44][N:40]([C:37]3[CH:38]=[CH:39][C:34]([O:33][C:32]([F:56])([F:31])[F:55])=[CH:35][CH:36]=3)[N:41]=2)=[CH:50][CH:49]=1)=[O:30])([CH3:3])[CH3:2]

참가 물질

10

반응물 6

HCID 10796Cesium carbonateHCID 125612-IsopropylanilineHCID 94429TriphosgeneHCID 105034IsocyanateHCID 516892Sodium BicarbonateHCID 904042683-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine

생성물 1

HCID 1186750951-(2-isopropylphenyl)-3-(3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propyl)urea수율 16%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

To 2-isopropylaniline (0.50 g, 3.7 mmol) and sodium bicarbonate (0.93 g, 11 mmol) in dichloromethane and water (36 mL, 2:1) was added triphosgene (0.55 g, 1.9 mmol) at 0° C. The reaction was stirred until complete conversion to the isocyanate, as observed by thin layer chromatography. The reaction was then diluted with dichloromethane (100 mL), and the organic layer was separated from the water layer and concentrated. The residue obtained was dissolved in acetonitrile (15 mL) and 3-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-1-amine (1.2 g, 3.4 mmol) and cesium carbonate (1.1 g, 3.4 mmol) were added. The reaction was stirred at room temperature for 16 hours. The reaction was quenched with water (50 mL) and extracted with dichloromethane (3×100 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using high pressure liquid chromatography provided the title compound as an off-white solid (0.26 g, 16%).

후처리

  1. customthe organic layer was separated from the water layer
  2. concentrationconcentrated
  3. customThe residue obtained
  4. customThe reaction was quenched with water (50 mL)
  5. extractionextracted with dichloromethane (3×100 mL)
  6. dry with materialThe organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash column chromatography

출처 및 근거

ORD 기록
ord-da2468c4aa91404388d54bd8211891cb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

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