Hydrochloric Acid → HCID 59321507, compound

HRID 2423492Notes

Reaction equation

HRID 2423492 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[C:26]([C:31]([O:33]C)=[O:32])[CH:25]=[CH:24]5)=[CH:17][CH:16]=3)=[C:11]([CH:35]([CH3:37])[CH3:36])[O:10][N:9]=2)=[C:6]([Cl:38])[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[C:26]([C:31]([OH:33])=[O:32])[CH:25]=[CH:24]5)=[CH:19][CH:20]=3)=[C:11]([CH:35]([CH3:36])[CH3:37])[O:10][N:9]=2)=[C:6]([Cl:38])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59321557HCID 59321557, compound

Product 1

HCID 59321507HCID 59321507, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 6-[4-({[3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (85 mg, 0.16 mmol) (from multiple batches) in THF (1.6 mL) was stirred as a 1 N aqueous sodium hydroxide solution (0.24 mL, 0.24 mmol) was added. The solution was allowed to stir at room temperature overnight. The solution was neutralized with 1 N HCl and concentrated. The residue was partitioned between ethyl acetate and brine. The organic layer was dried with MgSO4. The MgSO4 was slurried in dichloromethane, filtered and the combined filtrates were concentrated to yield 6-[4-({[3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a bright yellow foam (66 mg, 76% 0.12 ethyl acetate). 1H NMR (400 MHz, DMSO-d6): δ 13.37 (s, 1H), 8.54-8.51 (m, 2H), 8.28 (d, J=1 Hz, 1H), 8.17-8.08 (m, 3H), 7.80 (d, J=5 Hz, 1H), 7.74 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 4.96 (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; 534.0980 (M+H)+Obs.

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and brine
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationthe combined filtrates were concentrated

Sources & evidence

ORD record
ord-5274fc96ebf34d54b30a02f26a9b571c
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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