Hydrochloric Acid → 3-(4-Chloro-2-fluorobenzyl)-2-methyl-N-(5-methyl-1H-pyrazol-3-yl)-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-6-amine hydrochloride

HRID 597864Notes

Reaction equation

HRID 597864 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C:7]2[N:11]3[N:12]=[C:13]([NH:23][C:24]4[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=4)[CH:14]=[C:15]([CH2:16][N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:10]3=[N:9][C:8]=2[CH3:30])=[C:4]([F:33])[CH:3]=1.Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][C:7]2[N:11]3[N:12]=[C:13]([NH:23][C:24]4[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=4)[CH:14]=[C:15]([CH2:16][N:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[C:10]3=[N:9][C:8]=2[CH3:30])=[C:4]([F:33])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46213929Gandotinib

Product 1

HCID 468348643-(4-Chloro-2-fluorobenzyl)-2-methyl-N-(5-methyl-1H-pyrazol-3-yl)-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-6-amine hydrochlorideYield 206.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Combine 3-(4-chloro-2-fluorobenzyl)-2-methyl-N-(5-methyl-1H-pyrazol-3-yl)-8-(morpholinomethyl)imidazo[1,2-b]pyridazin-6-amine (0.1 g, 0.21 mmol) and 1,4-dioxane (10 mL) in a pear flask and place under nitrogen. Add hydrogen chloride (4 M in 1,4-dioxane, 0.053 mL, 1.0 equiv.) and let stir at RT under nitrogen for 1.5 h. Concentrate in vacuo then evaporate under vacuum from absolute ethanol two times. Dry overnight in a vacuum oven (60° C.) to give the title compound (0.11 g, 102%). LCMS (8 min)=470.0, M+1.

Workup

  1. concentrationConcentrate in vacuo
  2. customthen evaporate under vacuum from absolute ethanol two times
  3. customDry overnight in a vacuum oven (60° C.)

Sources & evidence

ORD record
ord-8dac3494801848e1a422cd7877bcf50b
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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