Sodium Carbonate → 4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone oxime

HRID 1483855Notes

Reaction equation

HRID 1483855 reaction equation
Cl.[NH2:2][OH:3].C([O-])([O-])=O.[Na+].[Na+].[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[N:21]3[N:22]=[C:23]([NH:26][CH:27]4[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1>O.CO>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[N:21]3[N:22]=[C:23]([NH:26][CH:27]4[CH2:32][CH2:31][C:30](=[N:2][OH:3])[CH2:29][CH2:28]4)[CH:24]=[CH:25][C:20]3=[N:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 712277284-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone

Product 1

HCID 893950924-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of hydroxylamine hydrochloride (15.3 mg, 0.22 mmol) and Na2CO3 (28 mg, 0.26 mmol) in water (0.7 mL) was added a solution of 4-((3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexanone (50 mg, 0.147 mmol) in MeOH (0.5 mL) at 0° C. The resulting mixture was stirred at room temperature for 1 h. LCMS showed the reaction was complete. The mixture was poured into water and extracted with EtOAc (50 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-HPLC and then by SFC to give EX. 8-92 (10 mg, 19%) as a white solid.

Workup

  1. extractionextracted with EtOAc (50 mL*3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep-HPLC and then by SFC
  6. customto give EX

Sources & evidence

ORD record
ord-6403151809e343458194f8e74f66f087
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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