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

HRID 2423472Notes

Reaction equation

HRID 2423472 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([CH2:11][C:12]1[C:16]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]=[C:30]([C:35]([O:37]CC)=[O:36])[CH:29]=[CH:28]4)=[CH:21][CH:20]=2)=[C:15]([CH:40]([CH3:42])[CH3:41])[O:14][N:13]=1)=[O:10].O1CCCC1.[OH-].[Na+].Cl>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([CH2:11][C:12]1[C:16]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:26]=[C:27]4[C:32](=[CH:33][CH:34]=3)[N:31]=[C:30]([C:35]([OH:37])=[O:36])[CH:29]=[CH:28]4)=[CH:23][CH:24]=2)=[C:15]([CH:40]([CH3:42])[CH3:41])[O:14][N:13]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321539Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593215206-[4-({[3-{[(2,6-Dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acidYield 100.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (6 mg, 0.01 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.020 mL, 0.020 mmol). The solution was heated in a microwave reactor at 90° C. for approximately 10 minutes and then 1 N hydrochloric acid (0.020 mL, 0.020 mmol) was added. The solution was concentrated and then dichloromethane and water were added. The layers were separated and the organic layer was dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)sulfinyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (6 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.38 (d, J=8 Hz, 1H), 8.23 (d, J=8 Hz, 2H), 8.04-8.01 (m, 2H), 7.68 (d, J=9 Hz, 2H), 7.31 (s, 3H), 7.07 (d, J=9 Hz, 2H), 5.14-4.99 (m, 2H), 4.84-4.59 (m, 2H), 3.24 (septet, J=7 Hz, 1H), 1.35 (d, J=7 Hz, 6H). LRMS (APCI) m/z 595 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. additiondichloromethane and water were added
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8886339ac62c4771860b9124120ac43a
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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