Trifluoroacetic acid → 4-Benzylamino-6-[(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxyamide

HRID 2035551Notes

Reaction equation

HRID 2035551 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15](CC2C=CC(OC)=CC=2)[C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:37][C:38]([NH2:40])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:17]=[N:18][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:37][C:38]([NH2:40])=[O:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731010HCID 131731010, compound

Product 1

HCID 1317310114-Benzylamino-6-[(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxyamideYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 mg of 4-benzylamino-6-[4-methoxybenzyl-(6-morpholinopyridin-3-yl)amino]pyridine-3-carboxyamide was dissolved in 0.5 mL of methylene chloride, to which 0.5 mg of trifluoroacetic acid was added, stirred at room temperature for 4 hours, and further heated at reflux at 70° C. for 8 hours. After cooling, the solvent was evaporated, saturated sodium bicarbonate in water was added to the residue, 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:methanol=10:1) and silica gel thin layer chromatography (chloroform:ammonium-saturated methanol=10:1) to obtain 1.2 mg (4 steps, yield 3%) of the title compound as a light brown solid.

Workup

  1. additionwas added
  2. temperaturefurther heated
  3. temperatureat reflux at 70° C. for 8 hours
  4. temperatureAfter cooling
  5. customthe solvent was evaporated
  6. additionsaturated sodium bicarbonate in water was added to the residue
  7. extractionextracted with chloroform
  8. washthe extract was washed with saturated saline
  9. dry with materialdried on anhydrous sodium sulfate
  10. customThe solvent was evaporated
  11. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1) and silica gel thin layer chromatography (chloroform:ammonium-saturated methanol=10:1)

Sources & evidence

ORD record
ord-b16678d5a0724fbb84bb804e19637e78
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

Loading…