2-Amino-6-benzothiazolol → 2-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol

HRID 71021

반응식

HRID 71021 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=O>CC(O)C>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([C:14]2[N:1]=[C:2]3[N:6]([CH:13]=2)[C:5]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:4]=2[S:3]3)=[CH:17][CH:18]=1)([O-:24])=[O:23]

참가 물질

4

반응물 2

HCID 334622-Amino-6-benzothiazololHCID 668402-Bromo-4'-nitroacetophenone

생성물 1

HCID 299332572-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol수율 65%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
0 °C

실험 절차

This product was prepared according to J. Med. Chem. 2009, 52, 7808-7816 with some modifications. A mixture of 2-amino-1,3-benzothiazol-6-ol (2.0 g, 12.18 mmol) and 2-bromo-4′-nitroacetophenone (2.97 g, 12.18 mmol) in IPA (40 ml) was heated to reflux for 24 h. The reaction mixture was then cooled to 0° C. and the resulting precipitate was filtrated and washed with IPA to afford 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-7-ol (65% c.y.). To a DMF (52 ml) solution of 2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazol-7-ol was added potassium carbonate (2.94 g) and 4-(2-chloroethyl)morpholine hydrochloride (1.97 g). The reaction mixture was heated to 85° C. and stirred at the same temperature for 48 h. Then it was poured into water (100 ml), filtered and washed with water and ethyl ether to give 7-(2-morpholin-4-yl-ethoxy)-2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole (86% c.y.). A mixture of 7-(2-morpholin-4-yl-ethoxy)-2-(4-nitrophenyl)imidazo[2,1-b][1,3]benzothiazole and ammonium chloride (0.77 g) in ethanol (50 ml) was heated to reflux, and then iron powder (3.0 g) was added. The mixture was refluxed for 5 h and then immediately filtered though Celite and washed with hot ethanol. The filtrate was concentrated, neutralized with saturated NaHCO3 solution and extracted with DCM. The organic solution was dried with Na2CO3 and the solvent was removed under reduced pressure to afford the desired product [4-(7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]benzothiazol-2-yl]aniline (32% c.y.).

후처리

  1. customThis product was prepared
  2. temperaturewas heated
  3. temperatureto reflux for 24 h
  4. filtrationthe resulting precipitate was filtrated
  5. washwashed with IPA

출처 및 근거

ORD 기록
ord-7b5ddd3a6bfb43ce8dc319713d57f9ca
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822698B2

연결된 노트

불러오는 중…