Tetrahydrofuran → 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide

HRID 2369594ノート

反応式

HRID 2369594 の反応式
C([Mg]Cl)(C)C.C1COCC1.C(O[C:14]([C:16]1[N:17]([S:29](=[O:34])(=[O:33])[N:30]([CH3:32])[CH3:31])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=1)=[O:15])C.Cl.[CH3:36][NH:37][O:38][CH3:39]>C(Cl)Cl.[NH4+].[Cl-]>[CH3:39][O:38][N:37]([CH3:36])[C:14]([C:16]1[N:17]([S:29](=[O:33])(=[O:34])[N:30]([CH3:31])[CH3:32])[N:18]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:20]=1)=[O:15]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 67958277HCID 67958277、化合物HCID 178418918HCID 178418918、化合物

生成物 1

HCID 866738982-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide収率 44%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

A 2M solution of isopropylmagnesium chloride in THF (1.9 mL, 3.8 mmol) was added to a stirred suspension of 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.45 g, 1.27 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.16 g, 1.65 mmol) in DCM (6.5 mL) under nitrogen at −78° C. The mixture was slowly allowed to warm to room temperature and stirred for 16 hours. The mixture was diluted with a saturated solution of NH4Cl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-dimethylsulfamoyl-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid methoxy-methyl-amide (0.2 g, 44% yield) as a colourless oil that solidified upon standing.

後処理

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents were evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 10/90)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-10c9f885dec746f396a1e1e4914d1f5e
出典データセット
uspto-grants-2014_04
特許番号
US08703946B2

反応ノート

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