Benzylamine → HCID 68482143, compound

HRID 2239900Notes

Reaction equation

HRID 2239900 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]2[C:10]3[N:11]([CH:23]=[CH:24][N:25]=3)[N:12]=[C:13]([CH2:15][N:16]3[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]3)[CH:14]=2)=[CH:5][CH:4]=1.C1COCC1.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.[OH-].[Na+]>[CH2:39]([NH:46][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][C:13]2[CH:14]=[C:9]([N:8]([CH2:7][C:6]3[CH:32]=[CH:33][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:10]3[N:11]([CH:23]=[CH:24][N:25]=3)[N:12]=2)[CH2:21][CH2:20]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 68483270HCID 68483270, compound

Product 1

HCID 68482143HCID 68482143, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a 2 dram vial was added 1-((8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazin-6-yl)methyl)piperidin-4-one (0.048 g, 0.109 mmol) from (1d), THF (0.362 mL) and benzylamine (0.013 mL, 0.120 mmol). The reaction was allowed to stir at room temperature for 1 hr. Sodium triacetoxyborohydride (0.092 g, 0.435 mmol) was then added and the reaction stirred for 48 hours at ambient temperature. The mixture was diluted with ethyl acetate and 1N NaOH solution and the layers separated. The organics were washed with water and the resulting aqueous solution was back-extracted with ethyl acetate (2×). The combined organics were collected, dried over Na2SO4, filtered and concentrated to provide 6-((4-(benzylamino)piperidin-1-yl)methyl)-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (0.05 g, 86% yield) which was subsequently used without further purification m/z=(532, M+1).

Workup

  1. stirringthe reaction stirred for 48 hours at ambient temperature
  2. customthe layers separated
  3. washThe organics were washed with water
  4. extractionthe resulting aqueous solution was back-extracted with ethyl acetate (2×)
  5. customThe combined organics were collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3feaaa209cd6450280bbeb2008bf01df
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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