Water → HCID 86635112, compound

HRID 69158Notes

Reaction equation

HRID 69158 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=O)=[CH:9][N:10]=2)[N:7]=1.[BH4-].[Na+].O.C([SiH](CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 4311764Sodium borohydrideHCID 86635113(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(4-methoxy-phenyl)-methanone

Product 1

HCID 86635112HCID 86635112, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(4-methoxy-phenyl)-methanone (Stage 3.2, 2.04 g, 7.1 mmol) was suspended in ethanol (20 mL) with sodium borohydride (140 mg, 3.6 mmol) and stirred at rt for 7 h. Then water was added and the precipitate formed was filtered off. The yellow solid obtained was dried and then dissolved in TFA (50 mL). Triethylsilane (2.85 mL, 17.7 mmol) was added to the solution and it was stirred at rt for 30 min. the RM was poured into ice water. It was extracted with EtOAc and washed with aqueous 1 N sodium hydroxide solution then with brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by chromatography with DCM and MeOH. The title compound was obtained As a white solid (tR 1.1 min (conditions 2), MH+=274).

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. customThe yellow solid obtained
  4. customwas dried
  5. dissolutiondissolved in TFA (50 mL)
  6. stirringwas stirred at rt for 30 min. the RM
  7. extractionIt was extracted with EtOAc
  8. washwashed with aqueous 1 N sodium hydroxide solution
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography with DCM and MeOH

Sources & evidence

ORD record
ord-f6b0ee18cfaf486195c4972917d2abe5
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

Loading…