1-bromohexan-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil. The mixture was refluxed for one hour the acetone was partially distilled to return to ambient temperature ice-cooled separated washed with ethyl ether The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction The extracts were washed with water saturated in sodium chloride dried filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil. The mixture was refluxed for one hour the acetone was partially distilled to return to ambient temperature ice-cooled separated washed with ethyl ether The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction The extracts were washed with water saturated in sodium chloride dried filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(1-Bromocyclopropyl)-4-butylthiazole 20 from 1-bromo-2-hexanone at 100° C. and a reaction time of 2 minutes. at 100° C. a reaction time of 2 minutes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil. The mixture was refluxed for one hour the acetone was partially distilled to return to ambient temperature ice-cooled separated washed with ethyl ether The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction The extracts were washed with water saturated in sodium chloride dried filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil. The mixture was refluxed for one hour the acetone was partially distilled to return to ambient temperature ice-cooled separated washed with ethyl ether The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction The extracts were washed with water saturated in sodium chloride dried filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil. The mixture was refluxed for one hour the acetone was partially distilled to return to ambient temperature ice-cooled separated washed with ethyl ether The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction The extracts were washed with water saturated in sodium chloride dried filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure as described in Example 2, making variations only as required to use 1-bromohexan-2-one in place of 1-bromobutan-2-one to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a white solid in 42% yield. 1H NMR (300 MHz, CDCl3) δ 7.72-7.48 (m, 4H), 7.43 (s, 1H), 7.35-7.32 (m, 1H), 6.71 (d, J=9.9 Hz, 1H), 4.02-3.83 (m, 2H), 3.53 (m, 2H), 3.37-3.3 (m, 4H), 2.74-2.69 (m, 2H), 1.76-1.61 (m, 2H), 1.48-1.3 (m, 2H), 0.91 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.4, 154.3, 146.8, 135.7, 134.4, 132.3, 129.4, 127.0, 126.8, 126.76, 126.7, 126.6, 126.2, 125.4, 125.3, 121.8, 113.6, 109.3, 46.5, 46.3, 46.2, 41.1, 31.5, 28.8, 22.4, 13.9. MS (ES+) m/z 432.3 (M+1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30.21 g of 2-picoline (0.32 mole) was slowly added to 83 g of 1-bromo-2-hexanone (0.46 mole) and stirred for 4 hours at ambient temperature. A viscous medium was obtained which was used as is for the next step. A viscous medium was obtained which

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(1-Bromocyclopropyl)-4-butylthiazole 20 from 1-bromo-2-hexanone at 100° C. and a reaction time of 2 minutes. at 100° C. a reaction time of 2 minutes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(1-Bromocyclopropyl)-4-butylthiazole 20 from 1-bromo-2-hexanone at 100° C. and a reaction time of 2 minutes. at 100° C. a reaction time of 2 minutes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(1-Bromocyclopropyl)-4-butylthiazole 20 from 1-bromo-2-hexanone at 100° C. and a reaction time of 2 minutes. at 100° C. a reaction time of 2 minutes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(1-Bromocyclopropyl)-4-butylthiazole 20 from 1-bromo-2-hexanone at 100° C. and a reaction time of 2 minutes. at 100° C. a reaction time of 2 minutes