Propanal → HCID 22024555, compound

HRID 1793106Notes

Reaction equation

HRID 1793106 reaction equation
[CH:1](=O)[CH2:2][CH3:3].S(=O)(=O)(O)O.[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[C:18]1[C:19]2[N:20]([C:24]([NH2:29])=[C:25]([CH2:27][CH3:28])[N:26]=2)[N:21]=[CH:22][CH:23]=1.[BH4-].[Na+].[OH-].[Na+].O1C[CH2:37][CH2:36][CH2:35]1>O>[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[C:18]1[C:19]2[N:20]([C:24]([N:29]([CH2:35][CH2:36][CH3:37])[CH2:1][CH2:2][CH3:3])=[C:25]([CH2:27][CH3:28])[N:26]=2)[N:21]=[CH:22][CH:23]=1

Participants

8

Reactant 6

HCID 527PropanalHCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22024329HCID 22024329, compound

Product 1

HCID 22024555HCID 22024555, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Propionaldehyde (0.435 mL, 6.0 mmol) and 3M sulfuric acid (2.01 mL, 6.0 mmol) were added to a solution of the crude 8-(2,4-dimethylphenyl)-2-ethylimidazo[1,2-b]pyridazin-3-amine (1.2 mmol) in tetrahydrofuran (10 mL) under ice-cooling, and sodium borohydride (182 mg, 4.8 mmol) was gradually added at the same temperature. After heating under stirring for 30 minutes, it was stirred at room temperature for 20 minutes, and neutralized by adding a 5N aqueous sodium hydroxide solution under ice-cooling. Water was added thereto, which was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:15) to give the title compound (42 mg, 10% (4 steps)) as yellow crystals.

Workup

  1. temperaturecooling
  2. temperatureAfter heating
  3. stirringit was stirred at room temperature for 20 minutes
  4. temperaturecooling
  5. extractionwhich was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:15)

Sources & evidence

ORD record
ord-f4ed6574379d403ca88d1259381799ea
Source dataset
uspto-grants-2006_07
Patent number
US07078405B2

Reaction notes

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