Water → HCID 86612813, compound

HRID 2370939Notes

Reaction equation

HRID 2370939 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]#[CH:9].[C:11]([O:15][C:16]([NH:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][C:26]([C:35]2[N:36]=[CH:37][NH:38][CH:39]=2)([C:31]([O:33][CH3:34])=[O:32])[C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].O>CN(C=O)C>[C:11]([O:15][C:16]([NH:18][C:19]1[N:24]=[CH:23][C:22]([CH2:25][C:26]([C:35]2[N:36]=[CH:37][N:38]([CH2:9][C:8]#[CH:7])[CH:39]=2)([C:31]([O:33][CH3:34])=[O:32])[C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 178499928HCID 178499928, compound

Product 1

HCID 86612813HCID 86612813, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

322 mg (0.99 mmol) of cesium carbonate and sowie 20 μl (0.27 mmol, 80% pure in toluene) of propargyl bromide were successively added to a solution of 100 mg (0.25 mmol) of dimethyl 2-(6-tert-butoxycarbonylaminopyridin-3-ylmethyl)-2-(1H-imidazol-4-yl)malonate (example 12d) in 2 ml of DMF. The mixture was stirred at RT for 3 h and then poured into water and extracted with EA. Purification by chromatography on silica afforded 27 mg of the title compound.

Workup

  1. extractionextracted with EA
  2. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-400a244858f542ffb32e976c49c04ee7
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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