Pyridine-4-carbonyl chloride → 2-(4-Isopropylpiperazin-1-yl)-6-(5-pyridin-4-yl-[1,2,4]oxadiazol-3-yl)benzothiazole

HRID 1619239노트

반응식

HRID 1619239 반응식
[OH:1][NH:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]2[N:9]=[C:10]([N:12]3[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)[S:11][C:7]=2[CH:6]=1)=[NH:4].[C:23](Cl)(=O)[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>C(O)(=O)C>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[S:11][C:7]3[CH:6]=[C:5]([C:3]4[N:4]=[C:23]([C:24]5[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=5)[O:1][N:2]=4)[CH:22]=[CH:21][C:8]=3[N:9]=2)[CH2:17][CH2:16]1)([CH3:19])[CH3:20]

참가 물질

4

반응물 2

HCID 417436Pyridine-4-carbonyl chlorideHCID 178456349HCID 178456349, 화합물

생성물 1

HCID 237288262-(4-Isopropylpiperazin-1-yl)-6-(5-pyridin-4-yl-[1,2,4]oxadiazol-3-yl)benzothiazole수율 11%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of N-hydroxy-2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxamidine (1.30 g, 4.07 mmol) in acetic acid (50 mL) was added isonicotinoyl chloride (1.42 g, 10.0 mmol). The reaction mixture was stirred overnight at room temperature and then heated at refluxed for 8 h. The reaction mixture was concentrated in vacuo and the residue was dissolved into 0.5 N hydrochloric acid (40 mL). The aqueous solution was extracted with diethyl ether (3×15 mL). The organic extracts were discarded and the aqueous phase was basified to pH 13 with 4 N sodium hydroxide and then extracted with ethyl acetate (4×10 mL). The combined organic extracts were evaporated and the residue was recrystallized from a mixture of CH2Cl2 and MeOH to give 175 mg (11%) of 2-(4-isopropylpiperazin-1-yl)-6-(5-pyridin-4-yl-[1,2,4]oxadiazol-3-yl)benzothiazole.

후처리

  1. temperatureheated
  2. temperatureat refluxed for 8 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved into 0.5 N hydrochloric acid (40 mL)
  5. extractionThe aqueous solution was extracted with diethyl ether (3×15 mL)
  6. extractionextracted with ethyl acetate (4×10 mL)
  7. customThe combined organic extracts were evaporated
  8. customthe residue was recrystallized from a mixture of CH2Cl2 and MeOH

출처 및 근거

ORD 기록
ord-a69a0a0eafad4a96b562d6eb853b76a7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772285B2

반응 노트

불러오는 중…