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

HRID 2423538Notes

Reaction equation

HRID 2423538 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][S:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([O:34]CC)=[O:33])[CH:26]=[CH:25]4)=[CH:18][CH:17]=2)=[C:12]([CH:37]([CH3:39])[CH3:38])[O:11][N:10]=1.C(O)C.[OH-].[Na+]>O1CCCC1>[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][S:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[N:28]=[C:27]([C:32]([OH:34])=[O:33])[CH:26]=[CH:25]4)=[CH:20][CH:21]=2)=[C:12]([CH:37]([CH3:39])[CH3:38])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 59321591Ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593215316-[4-({[3-(2,6-Dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylate (20 mg, 0.033 mmol) in tetrahydrofuran (0.33 mL) was placed in a microwave reaction vial followed by ethanol (0.17 mL) and 1 N sodium hydroxide (0.050 mL). The tube was sealed then heated to 100° C. for ten minutes. The reaction mixture was then concentrated and the residue partitioned between tetrahydrofuran and brine. 1 N hydrochloric acid (0.050 mL) was added. The organic layer was separated and concentrated to yield 17 mg (94%) of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}thio)phenyl]-2-quinolinecarboxylic acid as an orange solid. 1H NMR (400 MHz, d6-DMSO): δ 8.57 (d, J=9 Hz, 1H), 8.35 (s, 1H), 8.20-8.10 (m, 3H), 7.76 (d, J=8 Hz, 2H), 7.63 (d, J=7 Hz, 2H), 7.58-7.7.54 (m, 1H), 7.42 (d, J=8 Hz, 2H), 3.95 (s, 2H), 3.24 (septet, J=7 Hz, 1H), 1.16 (d, J=7 Hz, 6H). HRMS (ESI) C29H22Cl2N2O3S calculated: 549.0806 [M+H]+, found: 549.0813 [M+H]+.

Workup

  1. customThe tube was sealed
  2. concentrationThe reaction mixture was then concentrated
  3. customthe residue partitioned between tetrahydrofuran and brine
  4. addition1 N hydrochloric acid (0.050 mL) was added
  5. customThe organic layer was separated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d6f66e53b8647ff9bb7fb24151249da
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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