Hydrochloric Acid → HCID 68479389, compound

HRID 2239899Notes

Reaction equation

HRID 2239899 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]2[C:10]3[N:11]([CH:17]=[CH:18][N:19]=3)[N:12]=[C:13]([C:15]#[N:16])[CH:14]=2)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C(OCC)(=O)C>[NH2:16][CH2:15][C:13]1[CH:14]=[C:9]([N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:10]2[N:11]([CH:17]=[CH:18][N:19]=2)[N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 21225700DiisobutylaluminumhydrideHCID 68483194HCID 68483194, compound

Product 1

HCID 68479389HCID 68479389, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

To a 25 ml round bottom flask was added 8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-6-carbonitrile (0.62 g, 1.7 mmol) from (1a) and toluene (3.4 ml, 0.5 M) and the solution cooled to −5° C. To this was added dropwise, a 1.0 M solution of diisobutylaluminum hydride [DIBAL] in toluene (3.5 ml, 3.5 mmol) over a period of 10 minutes. The reaction was stirred at −5° C. for 1 hour and then warmed to room temperature and allowed to stir for an additional 2 hours. Dilute 1N HCl and ethyl acetate were added and the layers separated. The acidic aqueous layer was extracted 1 additional time with ethyl acetate and then basified with a 50% NaOH solution. The aqueous layer was extracted 2× with ethyl acetate and the combined organics were washed with brine (20 ml), dried over Na2SO4, filtered and concentrated in vacuo to provide crude 6-(aminomethyl)-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (0.44 g) which was used as such in the subsequent step. m/z=(360, M+1).

Workup

  1. additionTo this was added dropwise
  2. temperaturewarmed to room temperature
  3. stirringto stir for an additional 2 hours
  4. additionwere added
  5. customthe layers separated
  6. extractionThe acidic aqueous layer was extracted 1 additional time with ethyl acetate
  7. extractionThe aqueous layer was extracted 2× with ethyl acetate
  8. washthe combined organics were washed with brine (20 ml)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f0ac137c09341fda40f9f85380fb470
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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