Diisopropylethylamine → [(S)-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	[(S)-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 68592231	—

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 (50.1 mg, 0.11 mmol), HATU (50.1 mg, 0.12 mmol), and (R)-pyrrolidin-3-yl-carbamic acid tert butyl ester (22.8 mg, 0.12 mmol), DMF (3 ml) was added. The stirring mixture is treated with DIPEA (33 μL, 0.275 mmol) and stirred at RT. 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-3a46869840474199978d696d68f628d7
Source note	uspto-grants-2014_01