Diisopropylethylamine → (R)-tert-butyl (2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)(4-(2-(4-(3-((3-carbamoyl-4-((3-methoxyphenyl)amino)-8-methylquinolin-6-yl)sulfonyl)benzamido)phenyl)-1,3-dithiolan-2-yl)butyl)carbamate

https://huagongshe.com/reaction/1944963

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	3-(3-Carbamoyl-4-(3-methoxyphenylamino)-8-methylquinolin-6-ylsulfonyl)benzoic acid	HCID 57763288	—
Reactant	(R)-tert-butyl (4-(2-(4-aminophenyl)-1,3-dithiolan-2-yl)butyl)(2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)carbamate	HCID 86659090	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	(R)-tert-butyl (2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)(4-(2-(4-(3-((3-carbamoyl-4-((3-methoxyphenyl)amino)-8-methylquinolin-6-yl)sulfonyl)benzamido)phenyl)-1,3-dithiolan-2-yl)butyl)carbamate	HCID 86659121	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

DMAP (20 mg), HATU (110 mg, 0.29 mmol) and DIEA (0.15 mL, 0.87 mmol) were added to a stirring mixture of 3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzoic acid (144 mg, 0.29 mmol) and Intermediate 105 (0.18 g, 0.35 mmol) in NMP (3 mL). The reaction mixture was stirred overnight in an 80° C. oil bath and then purified by reverse-phase high performance liquid chromatography (RP-HPLC, acetonitrile/water/0.1% TFA) to provide, after concentration, the title compound as a dark yellow solid (90 mg, 27%). ES/MS calcd. for C60H71N6O10S3Si+ 1159.4. Found m/z=1159.6 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08394829B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-912412a04ad14000b286186eda145e7e
Source note	uspto-grants-2013_03