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

HRID 1944665Notes

Reaction equation

HRID 1944665 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-b20c4bfa6623456aa31c8d2e0d5f38b5
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

Loading…