Pyridine → 5-Bromo-2-(4-isopropylpiperazin-1-yl)benzothiazole

HRID 1619262Notes

Reaction equation

HRID 1619262 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](SC)=[N:7][C:6]=2[CH:12]=1.[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].N1C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([N:19]3[CH2:20][CH2:21][N:16]([CH:13]([CH3:15])[CH3:14])[CH2:17][CH2:18]3)=[N:7][C:6]=2[CH:12]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 780131-IsopropylpiperazineHCID 28012715-Bromo-2-(methylthio)benzo[d]thiazole

Product 1

HCID 595888005-Bromo-2-(4-isopropylpiperazin-1-yl)benzothiazoleYield 77%

Conditions

Temperature
160 °C

Procedure

A mixture of 5-bromo-2-(methylthio)benzothiazole (200 mg, 0.77 mmol), 1-isopropyl-piperazine (985 mg, 7.7 mmol) and pyridine (610 mg, 7.7 mmol) was heated at 160° C. for 36 h. The reaction mixture was concentrated under reduced pressure and the residue was extracted with dichloromethane (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (eluent: 2% EtOAc in Petroleum ether) to give 200 mg (77%) of 5-bromo-2-(4-isopropylpiperazin-1-yl)benzothiazole.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with dichloromethane (3×10 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: 2% EtOAc in Petroleum ether)

Sources & evidence

ORD record
ord-ee166a2858d941279dabeeb126d24493
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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