4-Methylmorpholine → 2-(6-Bromo-isoquinolin-1-yl carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/de/reaction/71729

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	4-Methylmorpholine	HCID 7972	—
Edukt	1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-	HCID 85083	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	1-Amino-6-bromoisoquinoline	HCID 22607616	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	2-(6-Bromo-isoquinolin-1-yl carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester	HCID 66620523	115,4%

Reaktionsschritte

To a mixture of 6-Bromo-isoquinolin-1-ylamine (0.80 g), Boc-L-proline (0.803 g), and 4-methylmorpholine (0.83 mL) in DMF (10 mL) was added HATU (1.39 g). Reaction mixture was stirred for 6 hours. Additional Boc-L-proline (0.803 g), 4-methylmorpholine (0.83 mL) and HATU (1.39 g) were added and reaction stirred overnight at ambient temperature and then concentrated. The residue was dissolved in ethyl acetate and washed with 10:1 H2O/saturated sodium bicarbonate solution, 5% lithium chloride solution, brine and dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 20 to 70% ethyl acetate/hexanes) to give 2-(6-Bromo-isoquinolin-1-yl carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.74 g): LCMS-ESI+: calc'd for C19H23BrN3O3: 421.31 (M+H+). Found: 419.8, 421.8 (M+H+).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08822430B2
Quelldatensatz	uspto-grants-2014_09
ORD ID	ord-131b828668184cd4aa33d7fb88522739
Quellennotiz	uspto-grants-2014_09