Diisopropylethylamine → (S)-1-Cyano-cyclopropanecarboxylic acid (1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-amide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1-Cyanocyclopropanecarboxylic acid	HCID 2733259	—
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	(S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride	HCID 86688559	—
Solvent	Dimethylformamide	HCID 6228	—
Product	(S)-1-Cyano-cyclopropanecarboxylic acid (1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethyl)-amide	HCID 71617628	—

Reaction Steps

To a mixture of 14 mg (0.13 mmol) 1-cyano-cyclopropanecarboxylic acid in 1 mL DMF are added 52 μL (0.30 mmol) DIPEA and 49 mg (0.13 mmol) HATU. The mixture is stirred for 10 min at rt. Subsequently a mixture of 36 mg (0.10 mmol) (S)-1-{4-[4-(4-ethoxy-phenyl)-piperidin-1-yl]-phenyl}-ethylamine hydrochloride (XII.1) in 1 mL DMF is added and stirring is continued for 6 h at rt. The crude mixture is directly purified by HPLC (Sunfire, narrow gradients, water (+0.1% TFA)/methanol) to yield the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765959B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-e5a3d201eb514b329bf0366ea9346ac5
Source note	uspto-grants-2014_07