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

HRID 2423470Notes

Reaction equation

HRID 2423470 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S: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]CC)=[O:35])[CH:28]=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:39]([CH3:41])[CH3:40])[O:13][N:12]=1.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][CH2:10][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:39]([CH3:41])[CH3:40])[O:13][N:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321572Ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593215486-[4-({[3-{[(2,6-Dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acidYield 107.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (5 mg, 0.008 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.04 mL, 0.04 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes and 1 N hydrochloric acid (0.04 mL, 0.04 mmol) was added. The mixture was concentrated and the residue was taken up with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)thio]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (5 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.44 (d, J=9 Hz, 1H), 8.29 (d, J=9 Hz, 1H), 8.21 (d, J=9 Hz, 1H), 8.10-8.07 (m, 2H), 7.70 (d, J=9 Hz, 2H), 7.34-7.14 (m, 3H), 7.10 (d, J=9 Hz, 2H), 5.08 (s, 2H), 4.16 (s, 2H), 3.20 (septet, J=7 Hz, 1H), 1.32 (d, J=7 Hz, 6H). HRMS (ESI) C30H24Cl2N2O4S calculated: 579.0912 (M+H)+, found: 579.0925 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ebd493b7d90144d9bd4309c2c522f1d7
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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