Water → HCID 56928279, compound

HRID 1773634Notes

Reaction equation

HRID 1773634 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:24][CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])[C:5]2[N:6]([C:8]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[C:13]([CH3:23])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH3:30][S-:31].[Na+].O>CS(C)=O>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[N:7]=[C:2]([S:31][CH3:30])[CH:3]=[C:4]([NH:24][CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])[C:5]4=[N:10][CH:9]=3)=[CH:12][C:13]=2[CH3:23])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86705349HCID 86705349, compound

Product 1

HCID 56928279HCID 56928279, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 83 mg (201 μmol) 4-{6-chloro-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl}-N-cyclopropyl-2-methylbenzamide which was prepared according to intermediate example 7a in 1.0 mL dimethyl sulfoxide were added 70 mg sodium methanethiolate and the mixture was heated under microwave irradiation at 70° C. for 1 hour. The mixture was poured into water and extracted with dichloromethane and methanol. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by recrystallisation to give 46.7 mg (55%) of the title compound.

Workup

  1. extractionextracted with dichloromethane and methanol
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of the solvent the residue
  5. customwas purified by recrystallisation

Sources & evidence

ORD record
ord-0842d4536cd14bd481741a22067354f7
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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