Diisopropylethylamine → Benzyl [(3S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-6-fluoro-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

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	Benzyl [(3S)-1-(3-aminopyridin-4-yl)piperidin-3-yl]carbamate	HCID 86726856	—
Reactant	3-{[(Benzyloxy)carbonyl]amino}-6-fluoro-7-vinylquinoline-2-carboxylic acid	HCID 86726864	—
Solvent	Dimethylformamide	HCID 6228	—
Product	Benzyl [(3S)-1-(3-{[(3-{[(benzyloxy)carbonyl]amino}-6-fluoro-7-vinylquinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate	HCID 86726866	86%

Reaction Steps

To a mixture of 3-{[(benzyloxy)carbonyl]amino}-6-fluoro-7-vinylquinoline-2-carboxylic acid (153.2 mg, 0.4182 mmol), benzyl [(3S)-1-(3-aminopyridin-4-yl)piperidin-3-yl]carbamate (151.1 mg, 0.4629 mmol) and HATU (485.8 mg, 1.278 mmol), DMF (4.0 mL) was added, followed by DIPEA (570.1 mg, 4.411 mmol). The reaction mixture was stirred at room temperature for 15 h, then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-10% MeOH in DCM) to give the sub-title compound (242.7 mg, 86%). LCMS calc. for C38H36FN6O5(M+H)+: m/z=675.3. found 675.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09278950B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-e0e0918bb2ea4b21b56a299d8cf11228
Source note	uspto-grants-2016_03