Water → HCID 131730983, compound

HRID 2035517Notes

Reaction equation

HRID 2035517 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH2:26][CH2:27][CH2:28]Cl)(=[O:25])=[O:24])=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:30][C:31]([NH2:33])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(NCC)C>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][S:23]3(=[O:25])=[O:24])=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:30][C:31]([NH2:33])=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 131730984HCID 131730984, compound2×

Product 1

HCID 131730983HCID 131730983, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8021DiethylamineSolvent

Conditions

Temperature
80 °C

Procedure

12 mg of 4-(benzylamino)-6-({4-[(3-chloropropylsulfonyl)amino]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 306) was dissolved in 1 mL of acetonitrile, to which 0.2 mL of diethylamine and 7 mg of potassium carbonate were added, and stirred at 80° C. for 1 hour. 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 column chromatography (chloroform:methanol=10:1) to obtain 12 mg (100%) of the title compound as a brown crystalline powder.

Workup

  1. additionwere 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 column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-b7f3c820577a41f7bb5ec78cb4954fcc
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

Loading…