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

HRID 84508

반응식

HRID 84508 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-11f202a7f24c4a8abe7555d752b5b622
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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