Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate → (2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Ethyl 5-amino-1,3,4-thiadiazole-2-carboxylate	HCID 2756556	—
Reactant	(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile	HCID 57634365	—
Product	(2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile	HCID 57756799	43.1%

Reaction Steps

In a similar manner to Example 87, (2S,4S)-1-[[N-(4-carboxybicyclo[2.2.2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (50.0 mg) and ethyl (5-amino-1,3,4-thiadiazole-2-carboxylate) (58.9 mg) were used to obtain (2S,4S)-1-[[N-[4-[N-(5-ethoxycarbonyl-1,3,4-thiadiazol-2-yl)amino]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (31.9 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07560569B2
Source dataset	uspto-grants-2009_07
ORD ID	ord-4ca57ffece0e4425a5a20b4045376281
Source note	uspto-grants-2009_07