1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11712792, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	1-(2-(Dimethylamino)ethyl)piperazine	HCID 2736229	—
Reactant	HCID 59836116	HCID 59836116	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 11712792	HCID 11712792	17.7%

Reaction Conditions

Temperature	70 °C

Reaction Steps

To a mixture of 3-[7-(2-Methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid (35 mg, 0.1 mmol), EDCI (77 mg, 0.40 mmol), HBTU (3.8 mg, 0.01 mmol) and diisopropylethylamine (175 μl, 1.0 mmol) in DMF (1 mL) was added 2-(dimethylamino)ethylpiperzine (55 μl, 0.3 mmol). The mixture was stirred at 70° C. for 5 hours before the solvents were removed. The resulting yellow oil was washed with water, dissolved in DMSO and purified on reverse phase HPLC to afford the title compound (8.6 mg, 12% over 2 steps) as yellow solid. MS: m/z 485.2 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08268994B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-77131841f9b14a6f8500e1cb9c0921c5
Source note	uspto-grants-2012_09