Diisopropylethylamine → HCID 178502304, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
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	(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid	HCID 10942966	—
Reactant	HCID 178427882	HCID 178427882	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 178502304	HCID 178502304	—

Reaction Steps

To a solution of 4-(4-bromo-phenyl)-2-((S)-4-methyl-2,5-dihydro-1H-pyrrol-2-yl)-1H-imidazole (1.10 g, 3.62 mmol) in DCM (50 mL) was added DIPEA (2.34 g, 18.1 mmol), (S)-2-methoxycarbonylamino-3-methyl-butyric acid (761 mg, 4.34 mmol) and HATU (1.65 g, 4.34 mmol). The mixture was stirred at RT overnight, washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered, concentrated and purified by column chromatography (10%-50% EtOAc in petroleum ether) to give the desired product, which was purified by supercritical fluid chromatography (SFC) [mobile phase A: supercritical CO2, phase B: methanol+0.05% diethylamine; flow rate: 80 mL/min] to give the title intermediate (750 mg, 45% yield). m/z): [M+H]+ calcd for C21H25BrN4O3 461.11, 463.11 found 461.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09066944B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-55f2a6b89f8941989a5e856fd65d88ca
Source note	uspto-grants-2015_06