Dimethylformamide → HCID 131730955, compound

HRID 2035497Notes

Reaction equation

HRID 2035497 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]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:10]=2)=[CH:4][CH:3]=1.Br[CH2:28][CH2:29][CH2:30][C:31]#[N:32].CN(C)C=O.C(=O)(O)[O-].[Na+]>O>[CH2:20]([NH:19][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:28][CH2:29][CH2:30][C:31]#[N:32])=[CH:7][CH:6]=2)[N:14]=[CH:13][C:12]=1[CH2:15][C:16]([NH2:18])=[O:17])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 214124-BromobutyronitrileHCID 516892Sodium BicarbonateHCID 131730943HCID 131730943, compound

Product 1

HCID 131730955HCID 131730955, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

99 mg of 6-[(4-aminophenyl)amino]-4-(benzylamino) pyridine-3-carboxyamide (the compound of Example 65) and 44 mg of 4-bromobutyronitrile were added to 0.2 mL of N,N-dimethylformamide, and stirred at 70° C. for 1.5 hour. To the reaction mixture, saturated sodium bicarbonate in water was added, 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=5:1) to obtain 59 mg (50%) of the title compound as a light brown powder.

Workup

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

Sources & evidence

ORD record
ord-65a6117e92bd46d2a7dff01ad2a22431
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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