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

HRID 1619239Notes

Reaction equation

HRID 1619239 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a69a0a0eafad4a96b562d6eb853b76a7
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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