Methyl iodide → (S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid

HRID 1403440ノート

反応式

HRID 1403440 の反応式
[C@@H:1]([NH:5][C:6]1[C:7]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=3[CH:24]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2].[H-].[Na+].[CH3:32]I>C1COCC1>[C@@H:1]([N:5]([CH3:32])[C:6]1[C:7]([C:20]2[O:21][C:22]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:23]=3[CH:24]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70665045(S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate

生成物 1

HCID 70664925(S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid収率 27%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-methyl 3-(sec-butylamino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylate (130 mg, 0.33 mmol) in THF (20 mL) was added NaH (52 mg, 1.32 mmol) and CH3I (188 mg, 1.32 mmol). The resulting solution was stirred overnight at room temperature and then the reaction mixture was poured into water/ice solution (20 mL). The mixture was evaporated until about 10 mL of water remained and adjusted to pH 5 with hydrochloric acid (1N). The product was collected by filtration to afford (S)-3-(sec-butyl(methyl)amino)-2-(5-fluorobenzofuran-2-yl)quinoxaline-6-carboxylic acid as a yellow solid (34.4 mg, 27%).

後処理

  1. customThe mixture was evaporated until about 10 mL of water
  2. filtrationThe product was collected by filtration

出典と根拠

ORDレコード
ord-2082e78426504d5db85602406d011a11
出典データセット
uspto-grants-2014_12
特許番号
US08912188B2

反応ノート

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