Diisopropylethylamine → HCID 11712792, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
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), EDCl (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	US07626021B2
Source dataset	uspto-grants-2009_12
ORD ID	ord-14a778a98a83429fb1e1f7acc4b9481d
Source note	uspto-grants-2009_12