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 1803899Notes

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

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 Feb. 1, 1998). 0.136 g of product is isolated after trituration in diisopropyl ether, filtering off and drying under reduced pressure.

Workup

customThe solvent is then evaporated off under reduced pressure
customthe oily residue is chromatographed on a column of silica gel
washeluting with a stepwise gradient of methanol and aqueous ammonia in dichloromethane (0/0/100 to Feb. 1, 1998)

Sources & evidence

ORD record: ord-5b880618ee39400ba1218b0632f09c90
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354405B2

Reaction notes

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