Figure - PMC

Skip to main content

An official website of the United States government

Here's how you know

Here's how you know

Official websites use .gov
A .gov website belongs to an official government organization in the United States.

Secure .gov websites use HTTPS
A lock ( ) or https:// means you've safely connected to the .gov website. Share sensitive information only on official, secure websites.

View full-text article in PMC

. 2016 Sep 15;116:63–72. doi: 10.1016/j.bcp.2016.07.018

Search in PMC
Search in PubMed
View in NLM Catalog
Add to search

© 2016 The Author(s)

This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

PMC Copyright notice

Fig. 2 — Synthetic pathway for the production of the potassium salt of CMF-019. Intermediates: (1) 4-fluoro-3-nitrobenzoic acid, (2) Methyl-4-fluoro-3-nitrobenzoate, (3) 3-(3-aminopentane)-4-nitrobenzylmethanoate, (4) Methyl-3-amino-4-(pentan-3-ylamino)benzoate, (5) Methyl-1-(pentan-3-yl)-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxylate, (6) 1-(Pentan-3-yl)-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole-5-carboxylic acid. Reagents and conditions: (a) SOCl₂, MeOH, (b) K₂CO₃, 3-aminopentane, DMF, (c) 5% Pd/C, H₂ (15 bar), MeOH, (d) 2-thiophene acetic acid, SOCl₂, DCM, (e) acetic acid, 140 °C (microwave), (f) NaOH, MeOH, 110 °C (microwave), (g) (i) HCTU, DIPEA, DMF, (ii) NaOH, MeOH, (h) KOH, 1,4-dioxane.