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

HRID 1909078Notes

Reaction equation

HRID 1909078 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-1cada48fa53a4ab0bc24f7868c7b5391
Source dataset
uspto-grants-2013_12
Patent number
US08598356B2

Reaction notes

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