Diisopropylethylamine → 5-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-(4-Methyl-1-piperazinyl)benzenemethanamine	HCID 2795568	—
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	5-Amino-2-fluoro-4-methylbenzoic Acid	HCID 79002145	—
Solvent	Dimethylformamide	HCID 6228	—
Product	5-Amino-2-fluoro-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide	HCID 86695683	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

A mixture comprising (2-(4-methylpiperazin-1-yl)phenyl)methanamine (413 mg, 2.010 mmol) and 5-amino-2-fluoro-4-methylbenzoic acid (step 2) (340 mg, 2.010 mmol) in DMF (3 ml) was treated with DIPEA (0.351 ml, 2.010 mmol) followed by HATU (764 mg, 2.010 mmol) and stirred at 25° C. for 24 hrs. The mixture was partitioned between water and EtOAc. The organic portion was washed with sat. aq. NaHCO3, 0.5 M LiCl and brine (each back extracted with EtOAc). The combined organic layers were dried (MgSO4), filtered and evaporated to dryness to give a pink oil. Purification by chromatography on silica eluting with 0-20% MeOH in DCM afforded the title compound;

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883819B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-1ae9bf6293c343478c2851864051ba76
Source note	uspto-grants-2014_11