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

HRID 1255772Notes

Reaction equation

HRID 1255772 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-114f0086238c4a7ab4941fe7c34b68e4
Source dataset
uspto-grants-2013_06
Patent number
US08461159B2

Reaction notes

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