1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58116824, compound

Participants

Role	Name	HCID	Charge
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	n,n-Dimethylpiperazine-1-carboxamide	HCID 712909	—
Reactant	4-Bromocrotonic acid	HCID 6436411	—
Reactant	(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine	HCID 58116912	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 58116824	HCID 58116824	24%

Reaction Steps

(2E)-4-Bromobut-2-enoic acid (106 mg, 0.64 mmol) and piperazine-1-carboxylic acid dimethylamide (107 mg, 0.68 mmol) were dissolved in DCM (5.0 mL), and DIPEA (111 mg, 0.85 mmol) was added. The mixture was stirred at rt for 2 h. Subsequently, the compound from Example 15A (150 mg, 0.43 mmol), DIPEA (55 mg, 0.43 mmol) and EDCI (82 mg, 0.43 mmol) were added. The reaction mixture was stirred at rt overnight. Then, water was added, and the mixture was extracted three times with DCM. The combined organic layers were dried over sodium sulfate. The solvent was removed in vacuo, and the residue was purified by preparative HPLC to yield 59 mg (24%) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08524722B2
Source dataset	uspto-grants-2013_09
ORD ID	ord-3db0a56a8e02415888246276a89874c5
Source note	uspto-grants-2013_09