Water → HCID 131730970, compound

HRID 2035507Notes

Reaction equation

HRID 2035507 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[CH:21][C:20]([CH2:23][C:24]([NH2:26])=[O:25])=[C:19]([NH:27][CH2:28][C:29]4[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=4)[CH:18]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C(=O)([O-])[O-].[K+].[K+].O.[CH3:44][NH2:45].C(O)C>>[F:35][C:33]1[CH:34]=[C:29]([CH:30]=[C:31]([F:36])[CH:32]=1)[CH2:28][NH:27][C:19]1[CH:18]=[C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][NH:45][CH3:44])[CH2:5][CH2:6]3)=[CH:15][CH:14]=2)[N:22]=[CH:21][C:20]=1[CH2:23][C:24]([NH2:26])=[O:25]

Participants

5

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22028356Methylamine ethanolHCID 131730971HCID 131730971, compound

Product 1

HCID 131730970HCID 131730970, compoundYield 15%

Conditions

Temperature
80 °C

Procedure

42 mg of 6-({4-[4-(2-chloroethyl)piperazin-1-yl]phenyl}amino)-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 250) was dissolved in a 30% methylamine-ethanol solution, to which 23 mg of potassium carbonate was added, and stirred at 80° C. for 8 hours. After cooling, water was added to the reaction mixture, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1), and crystallized by adding ether to obtain 8 mg (15%) of the title compound as a slight yellow solid.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with chloroform
  4. washthe extract was washed with saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)
  8. customcrystallized
  9. additionby adding ether

Sources & evidence

ORD record
ord-0d0f93ed07dd4a798b4de8b3bf1b792a
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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