1,2-Ethanediamine, N1,N1,N2-trimethyl- → N-(2-(dimethylamino)ethyl)-4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)-N-methylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Ethanediamine, N1,N1,N2-trimethyl-	HCID 67338	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	4-(3-(4-(4,6-Dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)benzoic acid	HCID 44516307	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	N-(2-(dimethylamino)ethyl)-4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)-N-methylbenzamide	HCID 44516311	50.2%

Reaction Steps

To the stirred solution of 4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2yl)phenyl)ureido)benzoic acid (150 mg; 0.297 mmol), Hunig's base (303 μL, 1.782 mmol), HBTU (563 mg, 1.485 mmol) in 2 mL of NMP was reacted according to example 68 with N1,N1,N2-trimethylethane-1,2-diamine (154 μL, 1.188 mmol) to give N-(2-(dimethylamino)ethyl)-4-(3-(4-(4,6-dimorpholino-1,3,5-triazin-2-yl)phenyl)ureido)-N-methylbenzamide as a white solid (88 mg, 50% yield); MS (ESI) m/z=590.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748421B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-e6b3fa39b666471e973b08b05b080e88
Source note	uspto-grants-2014_06