Diisopropylethylamine → 4-amino-5-chloro-2-fluoro-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	(3R)-1-Methyl-3-PyrrolidinaMine hydrochloride	HCID 53256048	—
Reactant	4-Amino-5-chloro-2-fluorobenzoic acid	HCID 68683933	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-amino-5-chloro-2-fluoro-N-[(3R)-1-methylpyrrolidin-3-yl]benzamide	HCID 68687588	77.6%

Reaction Steps

4-amino-5-chloro-2-fluorobenzoic acid (Intermediate 176; 300 mg, 1.58 mmol), HATU (903 mg, 2.37 mmol) and (3R)-1-methylpyrrolidin-3-amine di Hydrochloride (Intermediate 184; 325 mg, 2.37 mmol) were stirred in DMF (5 mL) and diisopropylethylamine (1.2 mL, 7.12 mmol) added. The mixture was stirred for 2 hours at room temperature and then absorbed on to an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and purified by column chromatography (5% ammonia in methanol/DCM) to yield the title compound as a pale orange solid (333 mg, 77%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07709471B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-2c7c543f60624e65a1fe74fe3bd894b3
Source note	uspto-grants-2010_05