Hydrochloric Acid → 1-(4,6-Dimethoxypyrimidin-2-yl)-3-(6-ethyl-2-methylimidazo[1,2-b]pyridazin-3-ylsulfonyl)urea

HRID 1946462Notes

Reaction equation

HRID 1946462 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([S:13]([NH2:16])(=[O:15])=[O:14])=[C:10]([CH3:12])[N:11]=2)[N:8]=1)[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[N:20]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C>[CH3:26][O:25][C:23]1[CH:24]=[C:19]([O:18][CH3:17])[N:20]=[C:21]([NH:27][C:28]([NH:16][S:13]([C:9]2[N:7]3[N:8]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]3=[N:11][C:10]=2[CH3:12])(=[O:14])=[O:15])=[O:29])[N:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 116084126-Ethyl-2-methylimidazo[1,2-b]pyridazine-3-sulfonamide

Product 1

HCID 230281271-(4,6-Dimethoxypyrimidin-2-yl)-3-(6-ethyl-2-methylimidazo[1,2-b]pyridazin-3-ylsulfonyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

As shown in the above reaction scheme, 6-ethyl-2-methylimidazo[1,2-b]pyridazin-3-ylsulfonamide (0.60 g, 2.50 mmol) and phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate (0.76 g, 2.76 mmol) were suspended in acetonitrile (10 ml) and stirred under ice-cooling, during which DBU (0.46 g, 3.02 mmol) was added thereto. The temperature of the reaction solution was increased to room temperature, and the mixture was stirred at the same temperature for 4 hours. The reaction solution was poured into ice-water (150 ml) and adjusted to pH 3 with conc. hydrochloric acid. The reaction mixture was stirred at room temperature for 5 minutes, and the precipitated crystals were washed with water, acetonitrile and diethyl ether in this order, and collected by filtration. The crystals were dried under reduced pressure to give the title compound as colorless crystals. The yield was 0.55 g (52%), and the melting point was 172 to 174° C.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at the same temperature for 4 hours
  3. stirringThe reaction mixture was stirred at room temperature for 5 minutes
  4. washthe precipitated crystals were washed with water, acetonitrile and diethyl ether in this order
  5. filtrationcollected by filtration
  6. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-a868702caa4645a2800c5364256bab3e
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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