Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Benzimidazole | HCID 5798 | — |
| Reactant | Trimethyl orthobeznoate | HCID 69720 | — |
| Reactant | Tolylboronic acid | HCID 79799 | — |
| Reactant | 1,2-Dimethoxy-4,5-dinitrobenzene | HCID 222989 | — |
| Reactant | Isopropyl 6-bromohexanoate | HCID 549816 | — |
| Reactant | HCID 11995863 | HCID 11995863 | — |
| Reactant | HCID 21937997 | HCID 21937997 | — |
| Reactant | HCID 21938036 | HCID 21938036 | — |
| Reactant | 5,6-Dimethoxy-2-phenyl-1H-benzimidazole | HCID 21938169 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 67363707 | HCID 67363707 | — |
Reaction Steps
4,5-Dimethoxy-1,2-dinitrobenzene was hydrogenated to the diamino compound according to general operating instructions 1, and said compound was cyclized with trimethyl orthobenzoate to 5,6-dimethoxy-2-phenyl-1H-benzimidazole (flash point 131-133° C.) as crude product according to general operating instructions 3. This benzimidazole derivative was reacted with 4-methylphenylboronic acid to 5,6-dimethoxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (flash point 145-148° C.) according to general operating instructions 14. After ether cleavage with hydrobromic acid according to general operating instructions 6 to 5,6-dihydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole (1H-NMR of hydrobromide (D6-DMSO): δ=2.42 ppm s (3H); 6.68 s (1H); 7.22 s (1H); 7.40-7.62 m (10H)), it was alkylated with 6-bromohexanoic acid isopropyl ester according to general operating instructions 8. 6-[[5-Hydroxy-1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]hexanoic acid isopropyl ester
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07329679B2 |
|---|
| Source dataset | uspto-grants-2008_02 |
|---|
| ORD ID | ord-ddc04dc5cea549a59aaf5ced3d13074b |
|---|
| Source note | uspto-grants-2008_02 |
|---|
