Lithium Hydroxide → 1-[(3,4-dimethylphenyl)methyl]-2-methyl-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylic acid
Reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:9]=[C:10]([C:11]([O-:13])=[O:12])[C:4]=2[N:3]=1.[OH-].[Li+].O1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:23][C:24]1[CH:4]=[C:10]([CH2:11][N:6]2[C:5]3[CH:7]=[C:8]([N:14]4[CH2:15][CH2:16][O:17][CH2:18][CH2:19]4)[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:4]=3[N:3]=[C:2]2[CH3:1])[CH:9]=[CH:8][C:25]=1[CH3:26]Participants
Conditions
- Temperature
- 50 °C
Procedure
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]+
Workup
- 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
Sources & evidence
- ORD record
- ord-433895d644b04c549ac82dba70b07857
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541411B2
Reaction notes
Loading…