Methanol → 6-(4-{[(3,5-Dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylic acid

HRID 2423481Notes

Reaction equation

HRID 2423481 reaction equation
[CH:1]1([C:6]2[C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[C:24]([C:29]([O:31]C)=[O:30])[CH:23]=[CH:22]5)=[CH:15][CH:14]=3)=[C:9]([CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[O:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+]>C1COCC1>[CH:1]1([C:6]2[C:10]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[C:24]([C:29]([OH:31])=[O:30])[CH:23]=[CH:22]5)=[CH:17][CH:18]=3)=[C:9]([CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[O:8][N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59321530Methyl 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylate

Product 1

HCID 593215186-(4-{[(3,5-Dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylic acidYield 844.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylate (65 mg, 0.13 mmol) in THF (1.3 mL) was placed in a microwave reaction tube. Methanol (0.7 mL) was added followed by 1.0 N sodium hydroxide (0.2 mL, 0.2 mmol) before the tube was sealed and stirred at room temperature for 30 minutes. The mixture was heated at 100° C. for 10 minutes. The solution was concentrated and the residue was suspended in water before neutralization with 1 N HCl. The resulting mixture was filtered and the sample was dried in a drying oven at 45° C. under reduced pressure with P2O5 to yield 6-(4-{[(3,5-dicyclopentyl-4-isoxazolyl)methyl]oxy}phenyl)-2-quinolinecarboxylic acid (0.53 g, 84%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.18-8.11 (m, 2H), 8.07 (d, J=9 Hz, 1H), 7.82 (d, J=9 Hz, 2H), 7.16 (d, J=9 Hz, 2H), 4.98 (s, 2H), 3.40-3.20 (m, overlapping H2O), 3.16-3.12 (m, 1H), 1.99 (m, 4H), 1.76-1.56 (m, 12H). HRMS C30H30N2O4 m/z 483.2278, (M+H)+Cal; 483.2277 (M+H)+Obs.

Workup

  1. customwas sealed
  2. temperatureThe mixture was heated at 100° C. for 10 minutes
  3. concentrationThe solution was concentrated
  4. filtrationThe resulting mixture was filtered
  5. dry with materialthe sample was dried in a drying oven at 45° C. under reduced pressure with P2O5

Sources & evidence

ORD record
ord-22b1fdd991154748b442e4006e1a3584
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…