1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
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	1-[(4-methylphenyl)sulfonyl]-3-oxo-2-Piperazineacetic acid	HCID 62034053	—
Reactant	(1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine	HCID 69078045	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-((1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide	HCID 11250383	—

Reaction Steps

To a 100 mL round bottom flask was added (1R)-6-(2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl)-1,2,3,4-tetrahydronaphthalen-1-amine (25.0 mg, 0.06 mmol), followed by 2-(3-oxo-1-tosylpiperazin-2-yl)acetic acid (50 mg, 0.016 mmol), dry CH2Cl2 (10 mL), HATU (12 mg, 0.03 mmol), EDCI (13 mg, 0.068 mmol) and hunig base (0.022 mL, 0.123 mmol). The resulting mixture was stirred at rt for 20 h. Removed solvent to dryness. Solvent was removed. The residue was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (97:3) gave final compound. MS m/z: 600.3 (M+H). Calc'd. for C32H33N5O5S -599.71.s

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07393852B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-e794a0f63a3e44afa4605e71b2873f10
Source note	uspto-grants-2008_07