Tetrahydrofuran → N-(2-chloro-4-fluorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84415

반응식

HRID 84415 반응식
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10](N(CC)CC)C.O1CCCC1.[S:22]1[C:26]2[C:27]3[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=3[O:29][CH2:30][CH2:31][C:25]=2[CH:24]=[C:23]1[C:36](Cl)=[O:37]>>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]([CH3:10])[C:36]([C:23]1[S:22][C:26]2[C:27]3[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=3[O:29][CH2:30][CH2:31][C:25]=2[CH:24]=1)=[O:37]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride

생성물 1

HCID 57900362N-(2-chloro-4-fluorophenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

실험 절차

To a solution of 2-chloro-4-fluoroaniline (0.110 g, 0.755 mmol) and triethylamine (0.105 mL, 0.755 mmol) in tetrahydrofuran (1.5 mL, 18 mmol) was added portion wise as a solid 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonyl chloride (0.100 g, 0.378 mmol). Reaction mix was stirred at room temperature with monitor for formation of desired product. The reaction was stirred overnight. The mixture containing the alkylated product was concentrated in vacuo to a solid residue, then taken into N,N-dimethylformamide (1.5 mL, 19 mmol) and treated with sodium hydride (0.0181 g, 0.755 mmol) followed by the addition of methyl iodide (0.0470 mL, 0.755 mmol). Reaction stirred at room temperature for about 1 hr with complete conversion to desired N-methyl derivative. After aqueous work up, the crude was taken into DMF at 100 mg/l mL and purified by preparative RP-HPLC to give 107. Yield=22% of theoretical. MS: (ESI+) 375

후처리

  1. customReaction
  2. additionmix

출처 및 근거

ORD 기록
ord-04f201a650f945e997c39f16493c2296
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

연결된 노트

불러오는 중…