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Phenyl 4-(methylsulfonamidomethyl)phenylcarbamate → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

HRID 1428711
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HRID 1428711 반응식
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=[C:31]([C:37]([F:40])([F:39])[F:38])[N:30]=2)[CH:24]=1>CN(C)C1C=CN=CC=1>[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH:36][C:14](=[O:22])[NH:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][CH:11]=3)=[CH:33][CH:32]=[C:31]([C:37]([F:39])([F:38])[F:40])[N:30]=2)[CH:24]=1
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참가 물질

4

반응물 2

HCID 86679364Phenyl 4-(methylsulfonamidomethyl)phenylcarbamateHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

생성물 1

HCID 71539427N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
50 °C

실험 절차

To a solution of phenyl 4-(methylsulfonamidomethyl)phenylcarbamate (59 mg, 0.18 mmol) acetonitrile (3 mL) was added 4-dimethylaminopyridine (23 mg, 0.18 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (49 mg, 0.18 mmol) at room temperature. The reaction mixture was heated to 50° C. for 16 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. 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 N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%).

후처리

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  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 to N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%)

출처 및 근거

ORD 기록
ord-826b80af24b242dbbeaa84c6270e1eb7
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937092B2

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