Preparation of 2‐Chloro‐1,3‐Bis(dimethylamino)Trimethinium Hexafluorophosphate

Abstract

2‐Chloro‐1, 3‐bis(dimethylamino)trimethinium hexafluorophosphate Chloroacetyl chloride Dimethylformamide Phosphorus oxychloride Hexafluorophosphoric acid

Profiling the Formation of 2-Chloro-N,N-dimethylamino Trimethinium Chloride Salt, a Key Intermediate in the Manufacturing Process of Etoricoxib

“…Representative Procedure. A DMF (321 mL, 4.14 mol) solution of chloroacetic acid (68.5 g, 0.725 mol) was heated to 75 °C followed by slow addition of POCl 3 (139.1 mL, 1.49 mol) over a 3 h period.…”

“…After the studies described in this paper, a reverse phase ion-pairing HPLC method was developed for analysis of CDT using a YMC Basic column and acetonitrile/4 mM heptane sulfonic acid sodium salt as mobile phase. See ref .…”

Development of a Scalable Route for a Highly Polar Heterocyclic Aminocyclopropyl Building Block

“…At this point, we realized that using an unsubstituted 1,3-dialdehyde synthon to give 17 was not possible, and alternative options needed to be explored. After considering many different reagents, we found 2-chloro-1,3-bis­(dimethylamino)­trimethinium hexafluorophosphate salt 20-PF 6 to be a suitable candidate thanks to its commercial availability on kg scale and its ease of handling as a bench-stable solid . In addition, we envisioned that chloride could be removed via hydro-dechlorination with H 2 in the same step as Cbz deprotection, which would make the overall reaction sequence quite elegant.…”

One-Pot Synthesis of 2,5-Disubstituted Pyrimidines from Nitriles

“…The resulting heterogeneous mixture containing the crude amidine ( 3b ) was cooled to 20 °C and 25 wt % NaOMe in MeOH (14.3 mL, 63.5 mmol) was charged. The mixture was then stirred for 30 min, and (Z)- N -(2-chloro-3-(dimethylamino)allylidene)- N -methylmethanaminium hexafluorophosphate(V) , (8.09 g, 90% w/w, 23.8 mmol) was charged to the above mixture in two portions at ambient temperature over approximately 30 min. The mixture was stirred for 3 h at ambient temperature and then concentrated under reduced pressure at 60 °C to a minimum stirrable volume (approximately 20 mL).…”