Dimethylformamide → HCID 66695584, compound

HRID 1773645Notes

Reaction equation

HRID 1773645 reaction equation
[CH:1]1([NH:4][C:5](=[O:38])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[O:35]C)[CH:19]=[C:20]([NH:21][CH2:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:37])[CH2:3][CH2:2]1.C[S-].[Na+].CN(C)C=O.[Cl-].[NH4+]>O>[CH:1]1([NH:4][C:5](=[O:38])[C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:16]4[N:17]=[C:18]([O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=5[OH:35])[CH:19]=[C:20]([NH:21][CH2:22][CH2:23][C:24]([F:27])([F:25])[F:26])[C:15]4=[N:14][CH:13]=3)=[CH:8][C:7]=2[CH3:37])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 4378561Sodium methanethiolateHCID 66691077HCID 66691077, compound

Product 1

HCID 66695584HCID 66695584, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 28.0 mg (53 μmol) N-cyclopropyl-4-{6-(2-methoxyphenoxy)-8-[(3,3,3-trifluoropropyl)amino]imidazo[1,2-b]pyridazin-3-yl}-2-methylbenzamide which was prepared according to example 223, 44.8 mg sodium methanethiolate and 350 μL N,N-dimethylformamide was heated under microwave irradiation for 30 minutes at 120° C. The mixture was poured into water, the pH was adjusted between 7 and 8 by addition of ammonium chloride and extracted with a mixture of dichloromethane and methanol. The combined organic phases were dried over sodium sulfate. After filtration and removal of solvent the residue was purified by chromatography to give 11.5 mg (40%) of the title compound.

Workup

  1. customwas prepared
  2. extractionextracted with a mixture of dichloromethane and methanol
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationAfter filtration and removal of solvent the residue
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-da6a2e1f1ea2434f91af482b3e2153a5
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

Loading…