Water → HCID 131730975, compound

HRID 2035511Notes

Reaction equation

HRID 2035511 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.C(N(CC)CC)C.[CH2:34]([N:36]([CH2:40][CH3:41])[C:37](Cl)=[O:38])[CH3:35].O>C(Cl)Cl.O1CCCC1>[CH2:20]([NH:19][C:11]1[CH:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:37](=[O:38])[N:36]([CH2:40][CH3:41])[CH2:34][CH3:35])=[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

7

Reactant 4

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 131730943HCID 131730943, compound

Product 1

HCID 131730975HCID 131730975, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

10 mg of 6-[(4-aminophenyl)amino]-4-(benzylamino) pyridine-3-carboxyamide (the compound of Example 65) was dissolved in 0.5 mL of methylene chloride and 0.2 mL of tetrahydrofuran, to which 33 mg of triethylamine and 41 mg of N,N-diethylcarbamoyl chloride were added, and stirred at room temperature for 3 days. To the reaction mixture, water was added, 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:methanol=5:1, developed twice) to obtain 9 mg (69%) of the title compound as a light brown crystalline powder.

Workup

  1. extractionextracted with chloroform
  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

Sources & evidence

ORD record
ord-f3aa497365464f6db9c2558f45b2fe78
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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