Lithium Hydroxide → 1-[(3,4-dimethylphenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylic acid

HRID 539192

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15]=[C:16]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH:17]=[C:18]([C:19]([O:21]C)=[O:20])[C:13]=3[N:12]=[C:11]2[CH3:29])[CH:5]=[CH:6][C:7]=1[CH3:8].[OH-].[Li+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]3[CH:15]=[C:16]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH:17]=[C:18]([C:19]([OH:21])=[O:20])[C:13]=3[N:12]=[C:11]2[CH3:29])[CH:5]=[CH:6][C:7]=1[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a mixture of methyl 1-[(3,4-dimethylphenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate (0.24 g, 0.61 mmol) in Tetrahydrofuran (THF) (10 mL) was added in lithium hydroxide (5.99 mL, 11.99 mmol). The reaction was stirred at 50° C. for 2 h. The reaction was cooled to room temperature. The organic solvent was removed in-vacuo. The precipitate was collected by filtration. Water (20 mL) was added in. The mixture was acidified with 1 N HCl. The resulting solid was filtered and washed with water and dried to give the product (0.16 g, 66%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18 (s, 6H), 2.58-2.75 (s, 3H), 3.06-3.22 (m, 4H), 3.71-3.82 (m, 4H), 5.55 (s, 2H), 6.94 (m, 1H), 7.04 (s, 1H), 7.11 (d, 1H, J=7.83 Hz), 7.52 (m, 2H). MS (ES+) m/e 380.2[M+H]+

Aufarbeitung

temperatureThe reaction was cooled to room temperature
customThe organic solvent was removed in-vacuo
filtrationThe precipitate was collected by filtration
additionWater (20 mL) was added in
filtrationThe resulting solid was filtered
washwashed with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-6195b8639061401181af5e1d26b94cc6
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08865912B2

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