HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-(Bromomethyl)-5-chloro-1-benzothiophene → 3-(5-Chloro-benzo[b]thiophen-2-ylmethyl)-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-3H-benzoimidazole-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-(Bromomethyl)-5-chloro-1-benzothiophene | HCID 13642606 | — |
| Reactant | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Reactant | 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester | HCID 68616159 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Product | 3-(5-Chloro-benzo[b]thiophen-2-ylmethyl)-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-3H-benzoimidazole-4-carboxylic acid | HCID 67011348 | — |
| Product | HCID 67012030 | HCID 67012030 | — |
Reaction Steps
1-(5-Chloro-benzo[b]thiophen-2-ylmethyl)-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid and 3-(5-Chloro-benzo[b]thiophen-2-ylmethyl)-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-3H-benzoimidazole-4-carboxylic acid were prepared by a procedure according to example 81 starting from 200 mg (0.58 mmol) 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester and 151.9 mg (0.58 mmol) 2-bromomethyl-5-chloro-benzo[b]thiophene. Hydrolysis of the resulting esters and purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave the title compounds as their formiates in form of white amorphous solids.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07741341B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-c32ae755381a41f3b8761c399aaf264e |
| Source note | uspto-grants-2010_06 |