Diisopropylethylamine → HCID 178502300, compound

https://huagongshe.com/reaction/2203126

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 178419349	HCID 178419349	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 178502300	HCID 178502300	—

Reaction Steps

To a solution of 4-(4-bromo-phenyl)-2-((S)-4-cyclopropyl-2,5-dihydro-1H-pyrrol-2-yl)-1H-imidazole (1.8 g, 5.45 mmol) in DCM (30 mL) was added DIPEA (3.52 g, 27.25 mmol), (S)-2-methoxycarbonylamino-3-methyl-butyric acid (1.14 g, 6.54 mmol) and HATU (2.49 g, 6.54 mmol). The mixture was stirred at RT overnight washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated. The resulting material was combined with the product of a separate batch prepared at the 0.61 mmol scale by the same process and purified by column chromatography (20%-50% EtOAc in petroleum ether) to give the desired product, which was purified by SFC separation to give the title intermediate (800 mg, 30% yield). m/z): [M+H]+ calcd for C23H27BrN4O3 487.13, 489.12 found 487.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365549B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-590ef763baa94991bff62d0112334865
Source note	uspto-grants-2016_06