Methanol → 4-(3,4-Dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylic acid

HRID 2238588Notes

Reaction equation

[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([O:25]C)=[O:24])[CH:13]=2)[CH2:3][CH2:2]1.CO.[OH-].[Li+]>O1CCCC1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([O:11][C:12]2[C:20]3[N:19]=[C:18]([CH3:21])[N:17]([CH3:22])[C:16]=3[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[CH:13]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of methyl 4-(3,4-dihydro-2H-chromen-4-yloxy)-1,2-dimethyl-1H-benzimidazole-6-carboxylate (1.0 g, 2.8 mmol, STEP 1) in methanol (20 mol) and tetrahydrofuran (30 mL) was added 4M lithium hydroxide aqueous solution (4 mL, 16 mmol) at room temperature. After stirring for 5 hours at 60° C., the reaction mixture was concentrated in vacuum. The residue was dissolved with water and acidified (pH=3) with 2M hydrochloric acid. The resulting precipitate was filtrated, and dried in vacuum to afford the title compound as a white solid (0.85 g, 89%):

Workup

concentrationthe reaction mixture was concentrated in vacuum
dissolutionThe residue was dissolved with water
filtrationThe resulting precipitate was filtrated
customdried in vacuum

Sources & evidence

ORD record: ord-85bbf96e3c1849efb6d5fdab2702e3dd
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718809B2

Reaction notes

Loading…