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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 1803899
Notes
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Reaction equation

HRID 1803899 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 Feb. 1, 1998). 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 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes