4-Methylmorpholine → HCID 68459274, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	Benzeneacetic acid, 3,5-difluoro-α-hydroxy-, (αS)-	HCID 6951479	—
Reactant	HCID 68457327	HCID 68457327	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 68459274	HCID 68459274	—

Reaction Steps

A solution of 0.14 g (0.4 mmol) of 2-amino-N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]propionamide and 0.08 g (0.4 mmol) of (S)-3,5-difluoromandelic acid (Garofalo, et al. Bioorg. Med. Chem. Lett. 2002, 12, 3051) in 5.0 mL of THF was stirred at rt as 0.06 g (0.4 mmol) of HOBT and 0.08 mL (0.7 mmol) of NMM was added followed by 0.90 g (0.5 mmol) of EDC.HCl. After 16 h, the reaction was quenched with 1M HCl and extracted with EtOAc. The organic layer washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated. Purification on silica gel using 4% Et3N-MeOH as eluant afforded N-[2-tert-butyl-5-(1-methyl-4-phenylpiperidin-4-yl)-2H-pyrazol-3-yl]-2-[2-(3,5-difluorophenyl)-2-hydroxyacetylamino]propionamide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07759382B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-45a5bac281f64693bdd22e2c926f55b2
Source note	uspto-grants-2010_07