Diisopropylethylamine → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3,3,3-Trifluoropropionic acid	HCID 2777972	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-(4-carbamoyl-3-((4-fluorophenyl)amino)-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidin-1-ium 2,2,2-trifluoroacetate	HCID 86729401	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Trifluoroacetic acid	HCID 6422	—
Product	1-(4-(Cyanomethyl)-1-(3,3,3-trifluoropropanoyl)piperidin-4-yl)-3-(4-fluorophenylamino)-1H-pyrazole-4-carboxamide	HCID 86729417	—

Reaction Steps

3,3,3-Trifluoropropanoic acid (0.009 mL, 0.1 mmol) and HATU (40 mg, 0.11 mmol) were combined in DMF (0.15 mL) and allowed to stir at ambient temperature for 5 minutes. A solution of 4-{4-carbamoyl-3-[(4-fluorophenyl)amino]-1H-pyrazol-1-yl}-4-(cyanomethyl)piperidinium trifluoroacetate (Intermediate #38-5) (30 mg, 0.066 mmol) in DMF (0.10 mL) was then added to the reaction mixture, followed by DIPEA (0.045 mL, 0.26 mmol). The resulting solution was allowed to stir at ambient temperature for 16 hours. The mixture was then purified directly by mass-triggered reverse-phase preparative HPLC (MeCN/water, with 0.1% v/v TFA modifier) to afford the title compound, Example #35-1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09328099B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-06c61c675a614ba2bd1d517aad6a3682
Source note	uspto-grants-2016_05