Water → HCID 9823755, compound

HRID 2415091Notes

Reaction equation

HRID 2415091 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:4][C:5]([CH3:9])=[N:6][C:7]=1[CH3:8].Cl[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26]([N+:29]([O-:31])=[O:30])=[CH:27][N:28]=2)[N:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:20]3[CH:21]=[CH:22][C:23]4[N:24]([C:26]([N+:29]([O-:31])=[O:30])=[CH:27][N:28]=4)[N:25]=3)=[CH:14][CH:13]=2)=[N:4][C:5]([CH3:9])=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 105359816-Chloro-3-nitro-imidazo(1,2-b)pyridazineHCID 22640009HCID 22640009, compound

Product 1

HCID 9823755HCID 9823755, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.0 g (30 mmol) of 4-[(5-chloro-2,6-dimethylpyrimidin-4-ylamino)methyl]phenol, 6.0 g (30 mmol) of 6-chloro-3-nitroimidazo[1,2-b]pyridazine and 20.7 g (150 mmol) of potassium carbonate in 150 ml of anhydrous dimethylformamide are heated at 80° C. with vigorous stirring for 1 h. After cooling to room temperature, the mixture is poured into water (1 l) and extracted with ethyl acetate (3×500 ml). The combined organic extracts are washed with water (500 ml), dried over sodium sulfate and concentrated. The beige solid (12.5 g) remaining is purified by chromatography on silica gel (mobile phase: toluene/acetone=2:1). The fractions with Rf=0.4 are collected and concentrated. The residue is suspended in 100 ml of methanol and the suspension is stirred for 30 min. Following filtration, this operation is repeated. After drying in a vacuum drying cabinet at 40° C., 7.8 g (61%) of the title compound are isolated as an almost white powder. m.p.: 203° C.

Workup

  1. extractionextracted with ethyl acetate (3×500 ml)
  2. washThe combined organic extracts are washed with water (500 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe beige solid (12.5 g) remaining is purified by chromatography on silica gel (mobile phase: toluene/acetone=2:1)
  6. customThe fractions with Rf=0.4 are collected
  7. concentrationconcentrated
  8. stirringthe suspension is stirred for 30 min
  9. filtrationfiltration
  10. customAfter drying in a vacuum
  11. customdrying cabinet at 40° C.

Sources & evidence

ORD record
ord-f61fe143627f47ce9883f22cbbb319a9
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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