Hydrochloric Acid → 7-(4-{[(5-Cyclobutyl-3-{[(2,6-dimethylphenyl)oxy]methyl}-4-isoxazolyl)methyl]oxy}phenyl)-3-isoquinolinecarboxylic acid

HRID 2423457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423457
[CH:1]1([C:5]2[O:9][N:8]=[C:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:19])[C:6]=2[CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:37]=[C:36]4[C:31]([CH:32]=[C:33]([C:38]([O:40]C)=[O:39])[N:34]=[CH:35]4)=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)[CH2:4][CH2:3][CH2:2]1.O1CCCC1.[OH-].[Na+].Cl>CO>[CH:1]1([C:5]2[O:9][N:8]=[C:7]([CH2:10][O:11][C:12]3[C:13]([CH3:19])=[CH:14][CH:15]=[CH:16][C:17]=3[CH3:18])[C:6]=2[CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:37]=[C:36]4[C:31]([CH:32]=[C:33]([C:38]([OH:40])=[O:39])[N:34]=[CH:35]4)=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321545Methyl 7-(4-{[(5-cyclobutyl-3-{[(2,6-dimethylphenyl)oxy]methyl}-4-isoxazolyl)methyl]oxy}phenyl)-3-isoquinolinecarboxylate

Produkt 1

HCID 593214847-(4-{[(5-Cyclobutyl-3-{[(2,6-dimethylphenyl)oxy]methyl}-4-isoxazolyl)methyl]oxy}phenyl)-3-isoquinolinecarboxylic acidAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl 7-(4-{[(5-cyclobutyl-3-{[(2,6-dimethylphenyl)oxy]methyl}-4-isoxazolyl)methyl]oxy}phenyl)-3-isoquinolinecarboxylate (50 mg, 0.091 mmol) in 2:1 tetrahydrofuran:methanol (3 mL) was added 1 N sodium hydroxide (0.14 mL, 0.14 mmol). The solution was heated in a microwave reactor at 100° C. for 500 seconds. Then 1 N hydrochloric acid (0.14 mL, 0.14 mmol) was added and the mixture was concentrated. The residue was taken up with ethyl acetate and water. The layers were separated and the organic layer was washed with water, dried over magnesium sulfate and concentrated to afford 7-(4-{[(5-cyclobutyl-3-{[(2,6-dimethylphenyl)oxy]methyl}-4-isoxazolyl)methyl]oxy}phenyl)-3-isoquinolinecarboxylic acid (41 mg, 84%). 1H-NMR (400 MHz, DMSO-d6) δ 9.41 (s, 1H), 8.61 (s, 1H), 8.49 (s, 1H), 8.24-8.18 (m, 2H), 7.85 (d, J=9 Hz, 2H), 7.16 (d, J=9 Hz, 2H), 7.00-6.90 (m, 3H), 5.06 (s, 2H), 4.90 (s, 2H), 4.01-3.90 (m, 1H), 2.39-2.30 (m, 4H), 2.14 (s, 6H), 2.10-2.00 (m, 1H), 1.90-1.89 (m, 1H). HRMS (ESI) C33H30N2O5 calculated: 535.2228 (M+H)+, found: 535.2228 (M+H)+.

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. customThe layers were separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-79e5ba80a50344609602fa04e8c24274
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960552B2

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