Triethylamine → HCID 67983359, compound

HRID 539763Notes

Reaction equation

HRID 539763 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:17])=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[N:7]=1.[F:18][C:19]1[CH:31]=[CH:30][C:22]([CH2:23][N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:21][CH:20]=1.C(N(CC)CC)C>C(#N)C>[F:18][C:19]1[CH:31]=[CH:30][C:22]([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([CH3:17])=[C:9]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[N:10]=4)[N:7]=3)[CH2:26][CH2:25]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7965631-(4-Fluorobenzyl)piperazineHCID 86667851HCID 86667851, compound

Product 1

HCID 67983359HCID 67983359, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A solution of 6-chloro-3-methyl-2-phenylimidazo[1,2-b]pyridazine (1.00 g, 4.35 mmol) and 1-(4-fluorobenzyl)piperazine (Sigma-Aldrich, 1.54 g, 4.35 mmol) in acetonitrile (50 mL) containing triethylamine (13.0 mmol) is heated at 180° C. in the microwave for 5 hours. The reaction mixture is concentrated to dryness and then purified via chromatography (hexanes to EtOAc) to afford the title product (0.82 g, 81%) as an off-white solid: Rf 0.30 (EtOAc); LCMS (m/z)=402.4 [M+H]+, tR=1.74 min. (compound same as Example 134)

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. custompurified via chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-2ac23239cbf348e1b58e07ce0d828860
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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