Diisopropylethylamine → n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	[(5R)-5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl]methanol	HCID 16108956	—
Reactant	(5,5-Dimethyl-3-oxo-1-(2,4,6-trimethylbenzene-sulfonyl)piperazin-2-yl)acetic acid	HCID 69078569	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide	HCID 72373799	—

Reaction Steps

[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)-yl]-acetic acid (600 mg, 1.6 mmol)and (5(R)-amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol (290 mg, 1.6 mmol) were dried by azeotroping with anhydrous toluene (3×1 mL) and dissolved in anhydrous DMF (10 mL). DIEA (0.55 mL, 3.2 mmol) and HATU (923 mg, 2.4 mmol) were added to the reaction and stirred for 18 h at RT. The reaction was diluted with EtOAc (30 mL), washed with dilute HCl (2×), 1N NaOH (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 5% MeOH in CH2Cl2) to provide the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07393852B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-defc9b4d229242cf841fbd2819affca2
Source note	uspto-grants-2008_07