Acetic Acid → N-(5-((1S,3S)-3-(5-acetamido-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(3-methoxyphenyl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	(3-Methoxyphenyl)acetic acid	HCID 15719	—
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	5,5'-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazol-2-amine)	HCID 86719119	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(5-((1S,3S)-3-(5-acetamido-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(3-methoxyphenyl)acetamide	HCID 86719123	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

A solution of 5,5′-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazol-2-amine) (50 mg, 0.18 mmol), acetic acid (1 eq), HATU (202 mg, 0.53 mmol), and DIPEA (73 mg, 0.57 mmol) in N,N-dimethylformamide (2 ml) was heated to 50° C. for 2 h, then 3-methoxy-2-phenylacetic acid was added. The mixture was heated at 50° C. overnight and then poured into water (20 ml), the precipitate was filtered to give the crude product. The crude product was purified by a standard method to give the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09029531B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-fbc2ecf2842b4db7be83c6e217c61c67
Source note	uspto-grants-2015_05