Hydrochloric Acid → 6-[4-({[3-{[(2,6-Dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

HRID 2423461Notes

Reaction equation

HRID 2423461 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([O:36]C)=[O:35])[CH:28]=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH2:10][C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([C:34]([OH:36])=[O:35])[CH:28]=[CH:27]4)=[CH:22][CH:23]=2)=[C:14]([CH:38]([CH3:40])[CH3:39])[O:13][N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321594Methyl 6-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593215236-[4-({[3-{[(2,6-Dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acidYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 6-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (23 mg, 0.043 mmol) in 2:1 tetrahydrofuran:methanol (0.75 mL) was added 1 N sodium hydroxide (0.064 mL, 0.064 mmol). The solution was heated in a microwave reactor at 120° C. for 500 seconds. The mixture was concentrated and water was added followed by 1 N hydrochloric acid (0.064 mL, 0.064 mmol). The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine and concentrated to afford of 6-[4-({[3-{[(2,6-dimethylphenyl)oxy]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow solid (14 mg, 62%). 1H-NMR (400 MHz, CDCl3) δ 8.43 (d, J=9 Hz, 1H), 8.29 (d, J=8 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 8.07 (m, 2H), 7.70 (d, J=9 Hz, 2H), 7.10 (d, J=9 Hz, 2H), 7.01-6.62 (m, 3H), 5.06 (s, 2H), 4.97 (s, 2H), 3.30 (septet, J=7 Hz, 1H), 2.23 (s, 6H), 1.39 (d, J=7 Hz, 6H). HRMS (ESI) C32H30N2O5 calculated: 437.2263 (M+H)+, found: 437.2263 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layers were washed with brine
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-65a98771bab24b5f96eb85eadbcde88d
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…