Diisopropylethylamine → [(R)-1-(2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine	HCID 1514397	—
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	{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid	HCID 24896589	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[(R)-1-(2-{1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester	HCID 68591551	—

Reaction Steps

To a vial charged with {1-[(5-Chloro-2,4-dimethoxy-phenylcarbamoyl)-methyl]-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}-acetic acid (50.9 mg, 0.11 mmol), HATU (49.4 mg, 0.12 mmol), and (R)-Pyrrolidin-3-yl-carbamic acid tert butyl ester (25.7 mg, 0.12 mmol), DMF (3 ml) is added. The stirring mixture is treated with DIPEA (33 μL, 0.275 mmol) and stirred at RT for 1 hour. Water is added to the mixture with stirring giving rise to a solid. This is filtered off and washed with water to afford the title compound, [M+H]+ 616

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08633211B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-6582fffdfb8c423f867b033f6fb89af3
Source note	uspto-grants-2014_01