Sodium hydride → 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide

HRID 1849501ノート

反応式

HRID 1849501 の反応式
[C:1]12([CH2:11][O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][C:14]=3[C:22]3[C:23]([O:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O1CCCC1>[C:1]12([CH2:11][O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH:19][S:33]([CH3:32])(=[O:35])=[O:34])=[O:18])=[CH:15][C:14]=3[C:22]3[C:23]([O:28][CH3:29])=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 867028454-(Adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide

生成物 1

HCID 867028464-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide収率 27.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide (0.39 g, 1.00 mmol) in tetrahydrofuran (30 mL) was added sodium hydride (0.09 g, 2.25 mmol). The reaction mixture was stirred at ambient temperature for 2 h, methanesulfonyl chloride (0.12 mL, 1.54 mmol) was added; stirring was continued for 46 h at ambient temperature and quenched by addition of 5% hydrochloric acid (1.0 mL). Diluted with ethyl acetate (100 mL) and washed with brine; dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography using 10% to 50% gradient ethyl acetate in hexanes to afford the title compound as a colorless solid (0.13 g, 27%): 1H NMR (300 MHz, CDCl3) δ 8.73 (br s, 1H), 8.21-8.17 (m, 1H), 7.88-7.83 (m, 1H), 7.78-7.65 (m, 1H), 7.55-7.50 (m, 1H), 7.00-6.93 (m, 2H), 3.88 (s, 3H), 3.53 (s, 2H), 3.40 (s, 3H), 1.90 (br s, 3H), 1.69-1.31 (m, 12H); MS (ES−) m/z: 469.1 (M−1).

後処理

  1. stirringstirring
  2. waitwas continued for 46 h at ambient temperature
  3. customquenched by addition of 5% hydrochloric acid (1.0 mL)
  4. additionDiluted with ethyl acetate (100 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by column chromatography

出典と根拠

ORDレコード
ord-5e3dcf1eb42d47538fd060753ba47994
出典データセット
uspto-grants-2015_02
特許番号
US08952169B2

反応ノート

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