Diisopropylethylamine → 2-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-n-indan-1-yl-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(R)-(-)-1-Aminoindan	HCID 2733933	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(5,5-Dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid	HCID 69078569	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-n-indan-1-yl-acetamide	HCID 59747953	—

Reaction Steps

[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)yl]-acetic acid (50 mg, 0.135 mmol) was dissolved in DMF (2.5 mL) and DIEA (0.1 mL) was added to make a solution. HATU (117 mg, 0.31 mmol) was added and after stirring for two min, (R)-(−)-indanamine (0.1 mL) was added and the mixture was stirred overnight. The solution was poured into EtOAc (50 mL), washed with saturated NH4Cl (1×50 mL), 1 N HCl (1×50 mL), saturated NaHCO3 (1×50 mL), and saturated brine (1×50 mL). The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo to provide a crude brown oil (140 mg). This crude oil was purified by SiO2 column chromatography (40 to 100% EtOAc in hexanes) to produce pure title compound. MS (APCI pos) 484 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07393852B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-544f455745ee42e79b804217634c23b5
Source note	uspto-grants-2008_07