2-Amino-3-chloropyridine → N-(3-chloropyridin-2-yl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84508

反応式

HRID 84508 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:9][Si](C)(C)N[Si](C)(C)C.[Na].[S:19]1[C:23]2[C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[O:26][CH2:27][CH2:28][C:22]=2[CH:21]=[C:20]1[C:33](Cl)=[O:34]>C1COCC1>[Cl:8][C:7]1[C:2]([N:1]([CH3:9])[C:33]([C:20]2[S:19][C:23]3[C:24]4[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=4[O:26][CH2:27][CH2:28][C:22]=3[CH:21]=2)=[O:34])=[N:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 6932672-Amino-3-chloropyridineHCID 45051731Sodium hexamethyidisilazaneHCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride

生成物 1

HCID 57900248N-(3-chloropyridin-2-yl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

An ice water cooled solution of 2-amino-3-chloropyridine (0.200 g, 0.755 mmol) in tetrahydrofuran (1.5 mL, 18 mmol) was reacted with a THF solution of 1 M sodium hexamethyldisilazane to give a clear solution. This reaction mix was stirred at cooled temperature for 30 minutes. Next, 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride (0.100 g, 0.378 mmol) was added portionwise as a solid. Reaction mix was stirred at room temperature with monitor for formation of desired product and concentrated in vacuo to a solid residue. This residue was taken into ethyl acetate and the organic was washed with water, then saline and dried (Na2SO4). The crude material was purified by MPLC on silica, eluting with 10% to 80% ethyl acetate/hexanes to give 128 mg N-(3-chloropyridin-2-yl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide, 34% of theoretical yield.

後処理

  1. customto give a clear solution
  2. additionThis reaction mix
  3. temperatureat cooled temperature for 30 minutes
  4. customReaction
  5. additionmix

出典と根拠

ORDレコード
ord-11f202a7f24c4a8abe7555d752b5b622
出典データセット
uspto-grants-2014_09
特許番号
US08846762B2

関連ノート

読み込み中…