Water → HCID 131730958, compound

HRID 2035499Notes

Reaction equation

HRID 2035499 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:32]=[CH:33][CH:34]=1)[CH2:7][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][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:28][C:29]([NH2:31])=[O:30])([O-:3])=[O:2].Cl.Cl[CH2:37][CH2:38][N:39]([CH2:42][CH3:43])[CH2:40][CH3:41].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:38]([N:39]([CH2:42][CH3:43])[CH2:40][CH2:41][N:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:13]3[N:12]=[CH:11][C:10]([CH2:28][C:29]([NH2:31])=[O:30])=[C:9]([NH:8][CH2:7][C:6]4[CH:32]=[CH:33][CH:34]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH:14]=3)=[CH:17][CH:18]=2)[CH2:27][CH2:26]1)[CH3:37]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 131730959HCID 131730959, compound

Product 1

HCID 131730958HCID 131730958, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

40 mg of 4-[(3-nitrobenzyl)amino]-6-{[4-(piperazin-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 224) was dissolved in 0.3 mL of N,N-dimethylformamide, to which 18.5 mg of 2-chloro-N,N-diethylethylamine hydrochloride and 25 mg of potassium carbonate were added, and stirred at room temperature for 3 hours. 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 thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 43 mg (88%) of the title compound as an orange crystalline powder.

Workup

  1. additionwere added
  2. extractionextracted with chloroform
  3. washthe extract was washed with saturated saline
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-043ebeb34eeb47dc8aeca4acd7bdb625
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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