Hydrochloric Acid → HCID 57472862, compound

HRID 501459Notes

Reaction equation

HRID 501459 reaction equation
[BH4-].[Na+].CO.[Cl-].[CH2:6]([N:10]1[C:14]2[C:15](=[O:20])[N:16]([CH3:19])[N:17]=[CH:18][C:13]=2[N:12]=[C:11]1[C:21]1[CH:26]=[CH:25][N+:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)[C:7]#[C:8][CH3:9].Cl>O>[CH2:6]([N:10]1[C:14]2[C:15](=[O:20])[N:16]([CH3:19])[N:17]=[CH:18][C:13]=2[N:12]=[C:11]1[C:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:23][CH:22]=1)[C:7]#[C:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 57472860HCID 57472860, compound

Product 1

HCID 57472862HCID 57472862, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.020 g of sodium borohydride was added to a 5 ml methanol solution of 0.060 g of 4-[1-(2-butynyl)-6-methyl-7-oxo-6,7-dihydro-1H-imidazo[4,5-d]pyridazin-2-yl]-1-(4-methoxybenzyl)pyridinium chloride, and the mixture was stirred for one hour. 15 ml of water and 0.1 ml of 5N hydrochloric acid were added to the solution to quench the reducing agent. Then, the solution was made alkaline with 1 ml of 5N sodium hydroxide, and extracted with 30 ml of ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.033 g of the title compound was obtained from the fraction eluted with methanol-ethyl acetate (1:19).

Workup

  1. customto quench the reducing agent
  2. extractionextracted with 30 ml of ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3cc3df1ec0d14597a79a0585df822fea
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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