1-(2-Hydroxyethyl)piperazine → 2-{4-[2-(4-Fluorophenyl)-3-(2-methoxypyrid-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanol

HRID 80732Notes

Reaction equation

HRID 80732 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[CH:19]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[N:26]1([CH2:32][CH2:33][OH:34])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(O)CCCC>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([N:29]4[CH2:30][CH2:31][N:26]([CH2:32][CH2:33][OH:34])[CH2:27][CH2:28]4)=[N:7][N:6]3[C:8]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([O:24][CH3:25])[CH:19]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 59406964HCID 59406964, compound

Product 1

HCID 251817232-{4-[2-(4-Fluorophenyl)-3-(2-methoxypyrid-4-yl)imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl}ethanolYield 43.3%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 0.25 g (0.70 mmol) of 6-chloro-2-(4-fluorophenyl)-3-(2-methoxypyrid-4-yl)imidazo-[1,2-b]pyridazine and 0.37 g (2.8 mmol) of 2-(piperazin-1-yl)ethanol in 6 mL of pentanol is stirred at 135° C. for 18 hours. The solvent is then evaporated off under reduced pressure and the oily residue is chromatographed on a column of silica gel, eluting with a stepwise gradient of methanol and aqueous ammonia in dichloromethane (0/0/100 to 2/1/98). 0.136 g of product is isolated after trituration in diisopropyl ether, filtering off and drying under reduced pressure.

Workup

  1. customThe solvent is then evaporated off under reduced pressure
  2. customthe oily residue is chromatographed on a column of silica gel
  3. washeluting with a stepwise gradient of methanol and aqueous ammonia in dichloromethane (0/0/100 to 2/1/98)

Sources & evidence

ORD record
ord-87a8fccc94de441592f1918692fa39bc
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Reaction notes

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