Methanol → HCID 131730956, compound

HRID 2035498Notes

Reaction equation

HRID 2035498 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[CH:13][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[C:11]([NH:19][CH2:20][C:21]3[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=3)[CH:10]=2)=[CH:4][CH:3]=1.Br[CH2:30][CH2:31][O:32][CH3:33].O.CO>CN(C)C=O>[F:27][C:25]1[CH:26]=[C:21]([CH:22]=[C:23]([F:28])[CH:24]=1)[CH2:20][NH:19][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:30][CH2:31][O:32][CH3:33])=[CH:7][CH:6]=2)[N:14]=[CH:13][C:12]=1[CH2:15][C:16]([NH2:18])=[O:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 809722-Bromoethyl methyl etherHCID 131730957HCID 131730957, compound

Product 1

HCID 131730956HCID 131730956, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

37 mg of 6-[(4-aminophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 67) and 14 mg of 2-bromoethyl methylether were dissolved in 0.3 mL of N,N-dimethylformamide, and stirred using a microwave reaction apparatus under an argon atmosphere at 120° C. for 20 minutes. After cooling, water was added to the reaction mixture, extracted with ethyl acetate, 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=20:1, developed twice) to obtain 13 mg (yield: 29%) of the title compound as a light yellow solid.

Workup

  1. customa microwave reaction apparatus under an argon atmosphere at 120° C. for 20 minutes
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  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

Sources & evidence

ORD record
ord-c30d14b1bab34e3aa9798fc01d614f52
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

Loading…