Diisopropylethylamine → HCID 178502469, 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 178503848	HCID 178503848	—
Solvent	Dimethylacetamide	HCID 31374	—
Product	HCID 178502469	HCID 178502469	83%

Reaction Steps

A mixture of (S)-2-methoxycarbonylamino-3-methyl-butyric acid (156 mg, 0.89 mmol) and HATU (407 mg, 1.07 mmol) was stirred in DMA (3.0 mL) for 10 min, then 4-(4-bromo-phenyl)-2-((2S,4S)-4-methylsulfanyl-pyrrolidin-2-yl)-1H-imidazole di-HCl (367 mg, 0.89 mmol; Preparation 18) and N,N-diisopropylethylamine (777.3 μL, 4.46 mmol) were added. The resulting mixture was stirred at RT overnight, concentrated, and purified by silica gel chromatography (0 to 90% EtOAc/hexane). Fractions with desired product were combined and concentrated to give the title intermediate (366 mg, 82% yield). (m/z): [M+H]+ calcd for C21H27BrN4O3S 495.10; 497.10. found 495.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09212168B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-7833fbc4830544b39c2eec6902137ba6
Source note	uspto-grants-2015_12