Diisopropylethylamine → N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)benzo[d]isoxazole-3-carboxamide

HRID 623576ノート

反応式

HRID 623576 の反応式
Cl.[F:2][C:3]([F:16])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH2:14])[CH3:13])=[CH:8][CH:7]=1.C(N(CC)C(C)C)(C)C.[O:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[C:28]([C:35](Cl)=[O:36])=[N:27]1>ClCCl.C(OCC)(=O)C>[F:16][C:3]([F:2])([F:15])[CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]([NH:14][C:35]([C:28]2[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:26][N:27]=2)=[O:36])[CH3:13])=[CH:8][CH:7]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 10419807Benzo[d]isoxazole-3-carbonyl ChlorideHCID 675094131-[6-(2,2,2-Trifluoroethoxy)-pyridin-3-yl]-ethylamine hydrochloride

生成物 1

HCID 67511565N-(1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)benzo[d]isoxazole-3-carboxamide収率 32%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (−)-1-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (20 mg, 0.078 mmol, Amine-1, single enantiomer) and N,N-diisopropylethylamine (0.054 mL, 0.31 mmol) in dichloromethane (0.5 mL) is added dropwise a solution of benzo[d]isoxazole-3-carbonyl chloride (17 mg, 0.094 mmol) in dichloromethane (0.5 mL) at room temperature. The reaction mixture is stirred at room temperature for 1 hour. The mixture is diluted with ethyl acetate (3 mL) and washed with water (1.5 mL). The organic layer is dried over sodium sulfate, and concentrated under reduced pressure. The residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate and then preparative LC-MS to give 9.1 mg (32% yield) of the title compound.

後処理

  1. washwashed with water (1.5 mL)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by column chromatography on NH-silica gel eluting with ethyl acetate

出典と根拠

ORDレコード
ord-b296a370e2024324b87d64f57abd9c76
出典データセット
uspto-grants-2016_04
特許番号
US09302991B2

反応ノート

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