Diisopropylethylamine → (S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	3,5-Diamino-6-chloro-pyrazine acid	HCID 6452119	—
Reactant	(S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride	HCID 117856338	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride	HCID 117856708	—

Reaction Steps

(S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride (60 mg, 0.1 mmol), 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (22 mg, 0.115 mmol) and N,N-Diisopropylethylamine (75 μl, 0.43 mmol) are dissolved in N,N-dimethylformamide (2 ml), 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (34 mg, 0.106 mmol) is added. The reaction is stirred at room temperature overnight and purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA). LC (method L): tR=1.15 min; Mass spectrum (ESI+): m/z=683 [M]+. IC50=0.025 μM

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09096548B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-0486180396294a588eaa0307bc3aeaef
Source note	uspto-grants-2015_08