4-Pyridineethanamine → HCID 9953325, compound

HRID 393265Notes

Reaction equation

HRID 393265 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:11]2[C:6]([CH:7]=[C:8]([C:20]([OH:22])=O)[C:9](=[O:19])[NH:10]2)=[CH:5][CH:4]=1.[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=1.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][C:20]([C:8]2[C:9](=[O:19])[NH:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=3[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:22])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 832754-PyridineethanamineHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 99045957-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 9953325HCID 9953325, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Methoxy-2-oxo-8-pentyloxy-1,2-dihydroquinoline-3-carboxylic acid (30.0 mg) obtained in Example 2-1, 2-pyridine-4-ylethylamine (36.0 mg), and 1-hydroxybenzotriazole hydrate (17.3 mg) were dissolved in dimethylformamide (2 ml), and 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimide hydrochloride (24.5 mg) was successively added to this solution while being cooled with ice. After the reaction solution was stirred at room temperature for 5 hours, ethyl acetate (3 ml) and a saturated aqueous solution of sodium hydrogencarbonate (3 ml) were added to this solution. The organic layer was separated and dried over anhydrous sodium sulfate, filtered to remove the desiccating agent, and concentrated under reduced pressure. The resultant residue was purified through column chromatography (eluent: a mixture of chloroform and methanol at a ratio of 25:1) to obtain the title compound (35 mg) as colorless crystals (Table 8).

Workup

  1. temperaturewhile being cooled with ice
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customto remove the desiccating agent
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified through column chromatography (eluent
  8. additiona mixture of chloroform and methanol at a ratio of 25:1)

Sources & evidence

ORD record
ord-d580c6657fa94e0db33e7441fa625a6a
Source dataset
uspto-grants-2004_10
Patent number
US06806276B2

Reaction notes

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