1-Methylpiperazine → {3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanone

Participants

Role	Name	HCID	Charge
Reactant	1-Methylpiperazine	HCID 53167	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	3-Aminobenzoate	HCID 3014145	—
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-(5-Bromo-thiophen-2-ylamino]-benzoic acid	HCID 86612625	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	{3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanone	HCID 16666647	79.1%

Reaction Steps

3-[4-(5-Bromo-thiophen-2-ylamino]-benzoic acid (20 mg, 0.048 mmol), prepared using method 2 (step 3) and 3-aminobenzoate, was combined with N-methylpiperazine (8.1 uL, 0.073 mmol), DIEA (29.2 uL, 0.168 mmol) and HATU (27.7 mg, 0.073 mmol) in a Smith microwave vial (0.2-5.0 mL) in 0.5 mL DMA. The mixture was micro waved at 90° C. for 900 s. The solution was diluted with 0.5 mL DMSO and purified by preparative HPLC to afford {3-[4-(5-Bromo-thiophen-2-yl)-pyrimidin-2-ylamino}-phenyl}-(4-methyl-piperazin-1-yl)methanone (17.8 mg, 79.1%) after lyophilization. MS: m/z 458 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07977481B2
Source dataset	uspto-grants-2011_07
ORD ID	ord-de61d50d355b48a18618f6a83f118801
Source note	uspto-grants-2011_07