Hydrochloric Acid → HCID 67411369, compound

HRID 2035534Notes

Reaction equation

HRID 2035534 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=2)=[CH:10][C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:5])C.Cl>C(O)C.O1CCCC1.[OH-].[Na+].O>[CH:14]1([CH2:13][NH:12][C:11]2[CH:10]=[C:9]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[N:8]=[CH:7][C:6]=2[C:4]([OH:5])=[O:3])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 58450547HCID 58450547, compound

Product 1

HCID 67411369HCID 67411369, compoundYield 106.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
100 °C

Procedure

108 mg of 4-[(cyclohexylmethyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxylic acid ethyl ester was dissolved in 4 mL of ethanol-tetrahydrofuran (1:1), to which 2 mL of 2 mol/L sodium hydroxide in water was added at room temperature, and stirred while heating at 100° C. for 2 hours. Under ice cooling, hydrochloric acid was added to acidify (about pH 4) the reaction mixture, extracted with chloroform, the extract was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated to obtain 108 mg of 4-[(cyclohexylmethyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxylic acid as a light brown crystalline powder. This was dissolved in 1 mL of N,N-dimethylformamide, to which 52 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 41 mg of 1-hydroxybenzotriazole monohydrate were added, and stirred at room temperature for 20 minutes. Then 1 mL of 28% ammonia water was added, and stirred at the same temperature for 16 hours. To the reaction mixture 10 mL of water was added, extracted with chloroform, and the extract was 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 44 mg (yield 37%) of the title compound as a light yellow crystalline powder.

Workup

  1. additionwas added at room temperature
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6197da3e7f464c149f75901ed92c2cd2
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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