Sodium Hydroxide → HCID 57917269, compound

HRID 69204

Reaction equation

HRID 69204 reaction equation
[H-].[Na+].[Cl-].[CH3:4][S+](C)(C)=O.[CH3:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]([C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[N:32]=[CH:31][CH:30]=[CH:29]5)=[CH2:25])=[CH:22][N:23]=3)[N:20]=2)[CH:12]=[N:11]1.[OH-].[Na+]>CS(C)=O>[CH3:9][N:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:24]4([C:26]5[CH:27]=[C:28]6[C:33](=[CH:34][CH:35]=5)[N:32]=[CH:31][CH:30]=[CH:29]6)[CH2:4][CH2:25]4)=[CH:22][N:23]=3)[N:20]=2)[CH:12]=[N:11]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 57917448HCID 57917448, compound

Product 1

HCID 57917269HCID 57917269, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

NaH 60% (96 mg, 2.41 mmol) was introduced in a round bottom flask and placed under nitrogen. A solution of trimethylsulfoxonium chloride (372 mg, 2.84 mmol) in DMSO (4 mL) was added slowly at rt. It was stirred for 30 min until H2 releasing was over. Then, a solution of 6-{1-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-vinyl}-quinoline (Example 155, 100 mg, 0.284 mmol) in DMSO (3 mL) was added dropwise. The RM was stirred for 1.5 h and then poured into 1 N NaOH. It was extracted twice with EtOAc and the organics were joined and washed with brine, dried over Na2SO4 and concentrated. The residue was again taken up in EtOAc and washed with water 4 times to take away remaining DMSO then washed with brine, dried over Na2SO4 and concentrated. It was purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to give the title compound as a light yellow solid (tR 1.0 min (conditions 1), MH+=367).

Workup

  1. stirringThe RM was stirred for 1.5 h
  2. extractionIt was extracted twice with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. washwashed with water 4 times
  7. washthen washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customIt was purified by preparative HPLC with acetonitrile and water (+0.1% TFA)

Sources & evidence

ORD record
ord-a6e186ac16f14178b17f68596db5173d
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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