Potassium Carbonate → HCID 131730973, compound

HRID 2035510Notes

Reaction equation

HRID 2035510 reaction equation
[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[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29]Cl)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:32][C:33]([NH2:35])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>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[CH2:27][CH2:26][N:25]([C:28](=[O:31])[CH2:29][N:8]([CH2:9][CH3:10])[CH2:1][CH3:2])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:32][C:33]([NH2:35])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131730974HCID 131730974, compound2×

Product 1

HCID 131730973HCID 131730973, compoundYield 119.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8021DiethylamineSolvent

Conditions

Temperature
80 °C

Procedure

25 mg of 4-(benzylamino)-6-({4-[4-(chloroacetyl)piperazin-1-yl]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 269) was dissolved in 2 mL of acetonitrile, to which 0.1 mL of diethylamine and 15 mg of potassium carbonate were added, and stirred at 80° C. for 1 hour. After cooling, the insoluble substances were filtered off, the solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 16 mg (59%) of the title compound as a light brown crystalline powder.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. filtrationthe insoluble substances were filtered off
  4. customthe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-3598b2d8ac7644feabd6c14a9e2658e8
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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