Cesium carbonate → 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-chloropyrimidine-4-carboxylic acid

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	5-chloro-2-(methylsulfonyl)pyrimidine-4-carboxylic acid	HCID 1241459	—
Reactant	N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride	HCID 86644320	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-chloropyrimidine-4-carboxylic acid	HCID 46836992	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of compound 1B (309 mg, 1 mmol), 5-chloro-2-methanesulfonyl-pyrimidine-4-carboxylic acid (236 mg, 1 mmol) and cesium carbonate (975 mg, 3 mmol) in 2 ml of DMSO was heated to 60° C. for 6 h. The product was precipitated out of solution by addition to water and collected by filtration. The crude material was chromatographed (SiO2, 20% methanol in dichloromethane) to afford title compound 123 as a white powder: LCMS (96% purity): m/z 465.9 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08232273B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-c843289ff31349798052f40aa1127a8e
Source note	uspto-grants-2012_07