Water → HCID 66691482, compound

HRID 1773644Notes

Reaction equation

HRID 1773644 reaction equation
[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH2:33]O)[CH:19]=[C:20]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:35])[CH2:3][CH2:2]1.C(N(S(F)(F)[F:43])CC)C.O>ClCCl>[CH:1]1([NH:4][C:5](=[O:36])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[CH2:33][F:43])[CH:19]=[C:20]([NH:21][CH2:22][C:23]([OH:26])([CH3:25])[CH3:24])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:35])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 66691195HCID 66691195, compound

Product 1

HCID 66691482HCID 66691482, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 329 mg (677 μmol) N-cyclopropyl-4-{6-[2-(hydroxymethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl}-2-methylbenzamide which was prepared according to example 220 in 13 mL dichloromethane at 3° C. were added 98 μL N-ethyl-N-(trifluoro-lambda4-sulfanyl)ethanamine. After stirring for 10 minutes, the solution was poured into water and the aqueous phase was extracted with dichloromethane. The combined organic phases were washed with sodium hydrogencarbonate solution and dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 28.6 mg (8%) of the title compound.

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. washThe combined organic phases were washed with sodium hydrogencarbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of solvent the residue
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-11330db027c04f5e8b3feacb783c437d
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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