HCID 131730996, compound → HCID 131730995, compound

HRID 2035529Notes

Reaction equation

HRID 2035529 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25](C(=O)C(F)(F)F)[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[N:12]=[CH:11][C:10]=2[CH2:34][C:35]([NH2:37])=[O:36])[CH:2]=1>CO.[OH-].[Na+].O>[N:22]1([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:13]3[N:12]=[CH:11][C:10]([CH2:34][C:35]([NH2:37])=[O:36])=[C:9]([NH:8][CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:14]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1

Participants

5

Reactant 1

HCID 131730996HCID 131730996, compound

Product 1

HCID 131730995HCID 131730995, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

66 mg of 4-[(pyridin-3-ylmethyl)amino}-6-({4-[4-(trifluoroacetyl)piperazin-1-yl]phenyl}amino}pyridine-3-carboxyamide (the compound of Example 354) was dissolved in 1 mL of methanol, to which 0.5 mL of 1 mol/L sodium hydroxide in water was added at room temperature, and stirred at the same temperature for 20 minutes. To the reaction mixture water was added, extracted with chloroform, and the extract was dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (chloroform:ammonia methanol=40:1 to 20:1) to obtain 51 mg (96%) of the title compound as a light brown crystalline powder.

Workup

  1. additionwas added at room temperature
  2. extractionextracted with chloroform
  3. dry with materialthe extract was dried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (chloroform:ammonia methanol=40:1 to 20:1)

Sources & evidence

ORD record
ord-1ba7bfed3bcb44e39285c5a262715c2a
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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