Benzenesulfonamide, 3-amino- → HCID 25263014, 화합물

HRID 1897557노트

반응식

HRID 1897557 반응식
[C:1]([C:5]1[S:9][C:8]([C:10]([O-:12])=O)=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:38][C:39]1[CH:40]=[C:41]([S:45]([NH2:48])(=[O:47])=[O:46])[CH:42]=[CH:43][CH:44]=1>CN(C=O)C.O>[C:1]([C:5]1[S:9][C:8]([C:10]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([S:45](=[O:47])(=[O:46])[NH2:48])[CH:40]=2)=[O:12])=[N:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57659748HCID 57659748, 화합물

생성물 1

HCID 25263014HCID 25263014, 화합물수율 31.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of lithium 5-tert-butyl-1,3,4-thiadiazole-2-carboxylate (0.2 g, 1 mmol) and HATU (0.38 g, 1.0 mmol) in DMF (5 mL) was stirred at room temperature for 10 minutes, then 3-amino-benzenesulfonamide (0. 17 g, 1.0 mmol) was added. The reaction was stirred for four hours, diluted with water, and extracted with ethyl acetate. The combined extracts were washed with brine and water, dried over sodium sulfate, and evaporated. The residue was purified by column chromatography on silica gel with 0-5% methanol in dichloromethane to give 5-tert-butyl-N-(3-sulfamoylphenyl)-1,3,4-thiadiazole-2-carboxamide (107 mg, 31% yield). LC/MS: m/z 341.1 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine and water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel with 0-5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-bb8f33e6c4214d50b888995402127117
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08519137B2

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