Triethylamine → 1-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
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	1-(4-Azetidin-3-yl-piperazin-1-yl)-2,2,2-trifluoro-ethanone	HCID 59625678	—
Reactant	1-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid	HCID 59625947	—
Solvent	Dichloromethane	HCID 6344	—
Product	1-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline	HCID 59625925	69.2%

Reaction Steps

To a solution of compound 1g (228 mg, 0.74 mmol), compound 25c (22 mg, 0.74 mmol), and Et3N (0.3 mL, 2.22 mmol) in CH2Cl2 (7 mL) was added HATU (338 mg, 0.89 mmol). The reaction mixture was stirred at room temperature for 18 h. The resultant mixture was diluted with CH2Cl2 and washed with aqueous NaHCO3. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 2% MeOH/EtOAc+0.5% Et3N) gave compound 25d (265 mg). LC/MS m/z (M+H+), 517.0 (M+2H+), 519.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08623858B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-5a55bb59a960427d8f3cef6e8694c615
Source note	uspto-grants-2014_01