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Hydrochloric Acid → 6-[4-({[5-Cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid

HRID 2423434
Notes
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Reaction equation

HRID 2423434 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:14]([Cl:15])=[CH:13][N:12]=[CH:11][C:10]=3[Cl:16])[C:5]=2[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]C)=[O:36])[CH:29]=[CH:28]4)=[CH:21][CH:20]=2)[CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[C:10]([Cl:16])=[CH:11][N:12]=[CH:13][C:14]=3[Cl:15])[C:5]=2[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)[CH2:2][CH2:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321467Methyl 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 593214656-[4-({[5-Cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid
Yield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (70 mg, 0.13 mmol) in 2:1 tetrahydrofuran:methanol (1.5 mL) was added 1 N sodium hydroxide (0.19 mL, 0.19 mmol). The solution was heated in a microwave reactor at 120° C. for 500 seconds. Then (0.19 mL, 0.19 mmol) 1 N hydrochloric acid was added and the solution was concentrated. The residue was taken up with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine and concentrated. The resulting solid was dried under a nitrogen stream at 45° C. over 48 hours to afford 6-[4-({[5-cyclopropyl-3-(3,5-dichloro-4-pyridinyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid as a yellow solid (53 mg, 78%). 1H-NMR (400 MHz, DMSO-d6) δ 13.37 (br s, 1H), 8.81 (s, 2H), 8.53 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.18-8.08 (m, 3H), 7.74 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 5.02 (s, 2H), 2.52-2.46 (m, 1H), 1.23-1.10 (m, 4H). HRMS (ESI) C28H19Cl2N3O4 calculated: 532.0825 [M+H]+, found: 532.0823 [M+H]+.

Workup

  1. concentrationthe solution was concentrated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated
  5. customThe resulting solid was dried under a nitrogen stream at 45° C. over 48 hours

Sources & evidence

ORD record
ord-12a5ed4e7aa2403e9718b40f07874c93
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960552B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes