Diisopropylethylamine → HCID 178459325, compound

https://huagongshe.com/reaction/1620743

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Propanol, 1-amino-2-methyl-	HCID 95102	—
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	HCID 178479765	HCID 178479765	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 178459325	HCID 178459325	23%

Reaction Steps

To a solution of N-[(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-2-oxo-2,5-dihydro-1,3-thiazol-4-yl]glycine hydrochloride (1.2 g), N-ethyl-N-(1-methylethyl)propan-2-amine (0.79 mL) and 1-amino-2-methylpropan-2-ol (0.40 g) in DMF (10 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.03 g), and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the obtained solid was recrystallized from ethyl acetate/heptane to give the title compound (294 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08772277B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-06f13264a268402c82c9f35c073e1935
Source note	uspto-grants-2014_07