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Sodium hydride → 4-[(4-But-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester

HRID 496578
ノート
印刷プレビュー

反応式

HRID 496578 の反応式
[H-].[Na+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[C:4]#[C:5][CH3:6].[CH2:19]([O:21][C:22]([C:24]1[C:25](Cl)=[C:26]2[C:32]([CH3:33])=[N:31][O:30][C:27]2=[N:28][CH:29]=1)=[O:23])[CH3:20]>CN1CCCC1=O>[CH2:19]([O:21][C:22]([C:24]1[C:25]([N:17]([S:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:3][C:4]#[C:5][CH3:6])=[CH:9][CH:10]=2)(=[O:15])=[O:16])[CH3:18])=[C:26]2[C:32]([CH3:33])=[N:31][O:30][C:27]2=[N:28][CH:29]=1)=[O:23])[CH3:20]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10847662Ethyl 4-chloro-3-methylisoxazolo[5,4-b]pyridine-5-carboxylateHCID 111607834-But-2-ynyloxy-N-methyl-benzenesulfonamide

生成物 1

HCID 697336794-[(4-But-2-ynyloxy-benzenesulfonyl)-methyl-amino]-3-methyl-isoxazolo[5,4-b]pyridine-5-carboxylic acid ethyl ester収率 90.2%

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒
2 回

実験手順

To a suspension of 0.105 g (0.63 mmol) of 60% sodium hydride in 8 mL of 1-methyl-2-pyrrolidinone was added 0.628 g (2.63 mmol) of the product of Example 5 and the resulting mixture was stirred for 30 minutes at room temperature. A solution of 0.601 g (2.50 mmol) of ethyl-4-chloro-3-methylisoxazolo[5,4-b]pyridine-5-carboxylate in 7 mL of 1-methyl-2-pyrrolidinone was added and the reaction was heated to 80-90° C. for 48 h. The reaction mixture was then concentrated in vacuo and the residue was diluted with dichloromethane. The organics were washed with water, 2N citric acid solution and brine, dried over Na2SO4, filtered through Magnesol® and concentrated in vacuo. The residue was triturated with ethyl acetate/hexanes and the resulting solid was filtered and dried in vacuo to provide 1.0 g (90%) of the product as a solid; m.p.85-90° C. Electrospray Mass Spec: 444 (M+H)+.

後処理

  1. temperaturethe reaction was heated to 80-90° C. for 48 h
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. additionthe residue was diluted with dichloromethane
  4. washThe organics were washed with water, 2N citric acid solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through Magnesol®
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ethyl acetate/hexanes
  9. filtrationthe resulting solid was filtered
  10. customdried in vacuo

出典と根拠

ORDレコード
ord-1843f4612dbe48459ec792811be30911
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06946473B2

反応ノート

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