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

HRID 1944665ノート

反応式

HRID 1944665 の反応式
[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]

参加物

4

反応物 2

HCID 417436Pyridine-4-carbonyl chlorideHCID 178456349HCID 178456349、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b20c4bfa6623456aa31c8d2e0d5f38b5
出典データセット
uspto-grants-2013_03
特許番号
US08394842B2

反応ノート

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