(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide

HRID 1428768노트

반응식

HRID 1428768 반응식
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)=[CH:10][CH:9]=1)(=[O:5])=[O:4])[CH3:2].[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=[C:32]([C:38]([F:41])([F:40])[F:39])[N:31]=2)[CH:25]=1>C(#N)C.CN(C)C1C=CN=CC=1>[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH:37][C:15](=[O:23])[NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][NH:6][S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:13][CH:12]=3)=[CH:34][CH:33]=[C:32]([C:38]([F:40])([F:39])[F:41])[N:31]=2)[CH:25]=1

참가 물질

5

반응물 2

HCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86680222Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate

생성물 1

HCID 71539386N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide수율 45%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (74 mg, 0.22 mmol) in acetonitrile (3 mL) was added 4-dimethylaminopyridine (27 mg, 0.22 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (59 mg, 0.22 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide (example 82) (50 mg, 45%).

후처리

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethylacetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-76637c4f762f45209e8f181ff608d86d
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937092B2

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