Benzenesulfonamide, 3-amino- → HCID 25263014、化合物

HRID 1897557ノート

反応式

HRID 1897557 の反応式
[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]

参加物

6

反応物 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、化合物

生成物 1

HCID 25263014HCID 25263014、化合物収率 31.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-bb8f33e6c4214d50b888995402127117
出典データセット
uspto-grants-2013_08
特許番号
US08519137B2

反応ノート

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