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

HRID 71021

反応式

HRID 71021 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
0 °C

実験手順

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.).

後処理

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

出典と根拠

ORDレコード
ord-7b5ddd3a6bfb43ce8dc319713d57f9ca
出典データセット
uspto-grants-2014_09
特許番号
US08822698B2

関連ノート

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