Cesium carbonate → HCID 12083063, compound

HRID 1168536Notes

Reaction equation

HRID 1168536 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][C:10]([C:12]1[C:21](=[O:22])[C:20]2[C:15](=[C:16](F)[CH:17]=[C:18]([I:23])[CH:19]=2)[N:14]([N:25]([CH2:27][CH:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:26])[CH:13]=1)=[O:11])[CH3:8]>CS(C)=O.O.C(O)(=O)C>[I:23][C:18]1[CH:17]=[C:16]2[C:15]3=[C:20]([C:21](=[O:22])[C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])=[CH:13][N:14]3[N:25]([CH3:26])[CH2:27][C:28]2([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:19]=1

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 12083062HCID 12083062, compound

Product 1

HCID 12083063HCID 12083063, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Cesium carbonate (0.367 g) is added to a solution of di(tert-butyl) 2-(((3-(ethoxycarbonyl)-8-fluoro-6-iodo-4-oxoquinolin-1(4H)-yl)(methyl)amino)methyl)malonate (Preparation 37, 0.517 g) in dimethylsulfoxide (5 mL) and the mixture is heated at 85° C. in an oil bath under a nitrogen atmosphere for 2 h. The mixture is cooled in an ice bath, diluted with 65 mL of water containing 2.5 mL of acetic acid, stirred, and the resultant yellow precipitate collected and dried in a vacuum oven to provide the title compound in 75% yield as a golden oil. Physical characteristics: 1H NMR (CDCl3) δ8.79, 8.54, 8.29, 4.40, 4.16, 2.78, 1.51, 1.41; MS (ESI+) m/z 599 (M+H)+; TLC (silica gel GF): Rf=0.59 acetone/CH2Cl2 (1/4).

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. customthe resultant yellow precipitate collected
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-640747517c6549e0a8c418852fb823dc
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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