Water → HCID 57917395, compound

HRID 69297Notes

Reaction equation

HRID 69297 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH:26]=[O:27])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1.O.[BH4-].[Na+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:11]([C:13]([CH2:16][C:17]4[CH:18]=[CH:19][C:20]5[N:21]([C:23]([CH2:26][OH:27])=[CH:24][N:25]=5)[CH:22]=4)=[CH:14][N:15]=3)[N:12]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57917323HCID 57917323, compound

Product 1

HCID 57917395HCID 57917395, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[6-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-ylmethyl]-imidazo[1,2-a]pyridine-3-carbaldehyde (Example 297, 50 mg, 0.140 mmol) was dissolved in MeOH (3 mL) and water (1 mL) then NaBH4 (2.6 mg, 0.070 mmol) was added. The RM was stirred at rt for 30 min. It was quenched with water and EtOAc. The precipitate formed was filtered off. The filtrate was concentrated then was triturated with MeOH. The salt was filtered off. The filtrate was concentrated and then triturated again with Et2O, The precipitate was filtered off and it was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM) to afford after evaporation of the solvent the title compound as a yellow solid (tR 0.6 min (conditions 2), MH+=360).

Workup

  1. customIt was quenched with water and EtOAc
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated
  5. customthen was triturated with MeOH
  6. filtrationThe salt was filtered off
  7. concentrationThe filtrate was concentrated
  8. customtriturated again with Et2O
  9. filtrationThe precipitate was filtered off
  10. customit was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, 0 to 20% MeOH in DCM)
  11. customto afford
  12. customafter evaporation of the solvent the title compound as a yellow solid (tR 0.6 min (conditions 2), MH+=360)

Sources & evidence

ORD record
ord-81cea682d7aa482a8a84fab7b37351ac
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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