2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 10093421, compound

HRID 750999Notes

Reaction equation

HRID 750999 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:26])=O)[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OC1C=CC2C(=CC=CC=2)[N:36]1C(OCC)=O)C>CN(C=O)C.[OH-].[NH4+]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[O:30][CH3:31])[N:10]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([NH2:36])=[O:26])[CH:19]=2)[CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 9931830HCID 9931830, compound

Product 1

HCID 10093421HCID 10093421, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 14923Ammonium HydroxideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyclopentyloxy-4-methoxy-N-(3-carboxyphenyl)-N-(3-pyridylmethyl)aniline (50 mg, 0.125 mmol) in 1 mL of DMF at room temperature was added 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) (50 mg, 0.20 mmol). The mixture was warmed slightly until everything was in solution, then cooled to room temperature and stirred for 1 h. 5 drops of ammonium hydroxide (28-30%) was added and the mixture was stirred for an additional hour. The mixture was partitioned between water (25 mL) and EtOAc (25 mL). The EtOAc fraction was separated, washed with brine (25 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography eluting with a linear gradient from 0% to 10% MeOH in EtOAc to give 3-cyclopentyloxy-4-methoxy-N-(3-aminocarbonylphenyl)-N-(3-pyridylmethyl)aniline (28 mg, 54% yield) as a white solid. EIMS (m/z) 418 (M+H)+.

Workup

  1. temperatureThe mixture was warmed slightly until everything
  2. stirringthe mixture was stirred for an additional hour
  3. customThe mixture was partitioned between water (25 mL) and EtOAc (25 mL)
  4. customThe EtOAc fraction was separated
  5. washwashed with brine (25 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography
  9. washeluting with a linear gradient from 0% to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-9ed3adcff5f34ddc837d564d2e5c633a
Source dataset
uspto-grants-2008_07
Patent number
US07405230B2

Reaction notes

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