Diisopropylethylamine → HCID 58557985、化合物

HRID 1969512ノート

反応式

HRID 1969512 の反応式
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.CCN(C(C)C)C(C)C.FC(F)(F)S([O-])(=O)=O.[N:25]1([S:30](N2C=C[N+](C)=C2)(=[O:32])=[O:31])[CH:29]=[CH:28][N:27]=[CH:26]1>CC#N>[F:2][C:3]1([F:7])[CH2:6][N:5]([S:30]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)(=[O:32])=[O:31])[CH2:4]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 117281493-(Imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate

生成物 1

HCID 58557985HCID 58557985、化合物収率 55.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 3,3-difluoroazetidine hydrochloride (1.00 g, 7.72 mmol) and DIEA (1.5 mL, 8.6 mmol) in MeCN (5 mL) was stirred for about 5 min and then was added to a solution of 1-(1H-imidazol-1-ylsulfonyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (4.20 g, 11.6 mmol) in MeCN (10 mL) at about 0° C. The reaction mixture was stirred at about 0° C. for about 1 h, and then warmed to ambient temperature and stirred for about 16 h. The reaction mixture was then concd under reduced pressure. The crude material was purified by flash chromatography on silica gel eluting with a gradient of 5-100% EtOAc in DCM to give 1-(3,3-difluoroazetidin-1-ylsulfonyl)-1H-imidazole (0.95 g, 55%) as a yellow solid: LC/MS (Table 1, Method c) Rt=1.16 min; MS m/z 224 (M+H)+.

後処理

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for about 16 h
  3. customThe crude material was purified by flash chromatography on silica gel eluting with a gradient of 5-100% EtOAc in DCM

出典と根拠

ORDレコード
ord-277da7afc80d4eaeabdcfba1e669ddc3
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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