Potassium Carbonate → HCID 22640006, compound

HRID 2415092Notes

Reaction equation

HRID 2415092 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=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+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([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:13]=2)=[N:4][C:5]([CH3:9])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 105359816-Chloro-3-nitro-imidazo(1,2-b)pyridazineHCID 22640019HCID 22640019, compound

Product 1

HCID 22640006HCID 22640006, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the method described in example 1, 7.9 g (30 mmol) of 3-[(5-chloro-2,6-dimethylpyrimidin-4-ylamino)methyl]phenol (from example B2), 6.08 g (30 mmol) of 6-chloro-3-nitroimidazo-[1,2-b]pyridazine and 20.9 g (150 mmol) of potassium carbonate are reacted in 125 ml of dimethylformamide. After chromatography on silica gel (mobile phase: gradient toluene/dioxane 5:1 to 2:1) and crystallization from methylene chloride/methanol and extraction with stirring from diisopropyl ether, 10.95 g (85%) of the title compound are isolated as a pale beige solid. m.p.: 222-223° C.

Workup

  1. customAfter chromatography on silica gel (mobile phase: gradient toluene/dioxane 5:1 to 2:1) and crystallization
  2. extractionfrom methylene chloride/methanol and extraction
  3. customare isolated as a pale beige solid

Sources & evidence

ORD record
ord-99b2baab5346431785805912d31bbea2
Source dataset
uspto-grants-2004_11
Patent number
US06818642B2

Reaction notes

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