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

HRID 1518419Notes

Reaction equation

HRID 1518419 reaction equation
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:14].[Cl:25][C:26]1[C:27]([C:36]([OH:38])=[O:37])=[N:28][C:29](S(C)(=O)=O)=[N:30][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][N:22]([C:29]1[N:28]=[C:27]([C:36]([OH:38])=[O:37])[C:26]([Cl:25])=[CH:31][N:30]=1)[CH2:21][CH2:20]2)=[O:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12414595-chloro-2-(methylsulfonyl)pyrimidine-4-carboxylic acidHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

Product 1

HCID 468369922-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-chloropyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

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].

Workup

  1. customThe product was precipitated out of solution by addition to water
  2. filtrationcollected by filtration
  3. customThe crude material was chromatographed (SiO2, 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c843289ff31349798052f40aa1127a8e
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…