Cesium carbonate → HCID 24988365, compound

HRID 643015Notes

Reaction equation

HRID 643015 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[C:23]4=[O:29])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:37][CH2:38][OH:39]>CS(C)=O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH2:37][CH2:38][OH:39])[C:23]4=[O:29])=[CH:20][CH:21]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 24988364HCID 24988364, compound

Product 1

HCID 24988365HCID 24988365, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

5-Chloro-N-((1-(4-(3-hydroxy-2-oxopyridin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (30 mg, 0.07 mmol, prepared as shown in EXAMPLE 61) was dissolved in 2 mL DMSO. To it were added cesium carbonate (69 mg, 0.21 mmol) and 2-bromoethanol (10 μL, 0.14 mmol). The mixture was stirred in a sealed tube at 70° C. for 30 min, and was directly subjected to reverse phase prep HPLC to isolate the title compound. MS found for C21H18ClN5O4S (M+H)+ 472.1, 474.1 (Cl pattern).

Sources & evidence

ORD record
ord-fff10f309b56447e8a9956821d896653
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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