Pyridine → Imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl ester

HRID 331115Notes

Reaction equation

HRID 331115 reaction equation
[N:1]1[CH:2]=[C:3]([NH2:10])[N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>CN(C=O)C.CCOC(C)=O>[C:21]1([O:20][C:18](=[O:19])[NH:10][C:3]2[N:4]3[N:5]=[CH:6][CH:7]=[CH:8][C:9]3=[N:1][CH:2]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 10702308Imidazo[1,2-b]pyridazin-3-amine

Product 1

HCID 58442681Imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of imidazo[1,2-b]pyridazin-3-ylamine (209 mg, 1.56 mmol) in dry DMF (5.0 mL) was added pyridine (382 μL, 4.68 mmol) and phenyl chloroformate (244 mg, 1.56 mmol). After 3 h at rt, the mixture was diluted with EtOAc (100 mL) and washed with saturated aqueous NaHCO3 (50 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give imidazo[1,2-b]pyridazin-3-yl-carbamic acid phenyl ester (285 mg, 72%). MS (ESI+): calcd for C13H10N4O2 m/z 254.08, found 255.3 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified (FCC)

Sources & evidence

ORD record
ord-fb265ad5553948099f0e42a99bed7eb3
Source dataset
uspto-grants-2014_11
Patent number
US08877769B2

Reaction notes

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