Water → 7-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid

HRID 2423396Notes

Reaction equation

HRID 2423396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:31]=[C:30]4[C:25]([CH:26]=[C:27]([C:32]([O:34]C)=[O:33])[CH:28]=[N:29]4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[C:12]([CH:36]([CH3:38])[CH3:37])[O:11][N:10]=1.C1COCC1.O.[OH-].[Na+]>CCO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:31]=[C:30]4[C:25]([CH:26]=[C:27]([C:32]([OH:34])=[O:33])[CH:28]=[N:29]4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[C:12]([CH:36]([CH3:38])[CH3:37])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321510Methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate

Product 1

HCID 533268927-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To 47 mg (0.09 mmol) of methyl 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate in a mixture of 3 mL of EtOH, 1 mL THF and 1 mL H2O was added 35 mg (0.86 mmol) of NaOH and the mixture stirred at 50° C. for 16 hr. The mixture was concentrated to ⅓ volume then added dropwise to a a stirred solution of 10 mL of 0.5 M HCl (aq.). The resulting solids were collected by suction filtration, washed with water then dried to yield 32 mg (70%) of 7-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 8.97 (s, 1H), 8.24-8.21 (m, 2H), 7.99 (d, J=8 Hz, 1H), 7.76 (d, J=8 Hz, 2H), 7.63-7.61 (m, 2H), 7.55-7.52 (m, 1H), 6.93 (d, J=9 Hz, 2H), 4.88 (s, 2H), 3.50-3.44 (septet, J =7 Hz, 1H), 1.33 (d, J=7 Hz, 6H). ESI-LCMS m/z 534 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthen added dropwise to a a stirred solution of 10 mL of 0.5 M HCl (aq.)
  3. filtrationThe resulting solids were collected by suction filtration
  4. washwashed with water
  5. customthen dried

Sources & evidence

ORD record
ord-1784abe5297d4f469df4d1cc406c1ee4
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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