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

HRID 2423477Notes

Reaction equation

HRID 2423477 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:38])[C:7]=1[C:8]1[C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]=[C:26]([C:31]([O:33]C)=[O:32])[CH:25]=[CH:24]4)=[CH:17][CH:16]=2)=[C:11]([CH:35]([CH3:37])[CH3:36])[O:10][N:9]=1.CO.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:38])[C:7]=1[C:8]1[C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]4[C:28](=[CH:29][CH:30]=3)[N:27]=[C:26]([C:31]([OH:33])=[O:32])[CH:25]=[CH:24]4)=[CH:17][CH:16]=2)=[C:11]([CH:35]([CH3:36])[CH3:37])[O:10][N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59321521Methyl 6-[4-({[3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593214616-[4-({[3-(3,5-Dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 6-[4-({[3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (98 mg, 0.18 mmol) in THF (1.8 mL) was placed in a microwave reaction tube. Methanol (0.9 mL) was added followed by 1.0 N sodium hydroxide (0.27 mL, 0.27 mmol) before the tube was sealed and heated at 100° C. for 600 seconds. The solution was neutralized with 1 N HCl. The resulting mixture was partitioned between brine and ethyl acetate. The organic layer was separated and concentrated to yield 6-[4-({[3-(3,5-dichloro-4-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow powder (0.08 g, 80% as 0.25 ethyl acetate). 1H NMR (400 MHz, DMSO-d6): δ 13.37 (br s, approximately 1H), 8.81 (s, approximately 2H), 8.53 (d, J=9 Hz, 1H), 8.27 (s, 1H), 8.17-8.08 (m, 3H), 7.73 (d, J=9 Hz, 2H), 6.89 (d, J=9 Hz, 2H), 4.97 (s, 2H), 3.49 (septet, J=7 Hz, 1H), 1.34 (d, J=7 Hz, 6H). HRMS C28H21N3O4Cl2 m/z 534.0982 (M+H)+Cal; 534.0981 (M+H)+Obs.

Workup

  1. customwas sealed
  2. customThe resulting mixture was partitioned between brine and ethyl acetate
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f9442cab9d240b8be136ca5afdfdb66
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

Loading…