Dimethyl Sulfoxide → Lenvatinib

HRID 557486Notes

Reaction equation

HRID 557486 reaction equation
CS(C)=O.[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](Cl)=[CH:12][CH:13]=[N:14]2)=[CH:9][C:8]=1[C:18]([NH2:20])=[O:19].[Cl:21][C:22]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:30]([NH:32][CH:33]1[CH2:35][CH2:34]1)=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:21][C:22]1[CH:27]=[C:26]([CH:25]=[CH:24][C:23]=1[NH:29][C:30]([NH:32][CH:33]1[CH2:34][CH2:35]1)=[O:31])[O:28][C:11]1[C:10]2[C:15](=[CH:16][C:7]([O:6][CH3:5])=[C:8]([C:18]([NH2:20])=[O:19])[CH:9]=2)[N:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 229364184-Chloro-7-methoxyquinoline-6-carboxamideHCID 23135084ME-92

Product 1

HCID 9823820LenvatinibYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To dimethylsulfoxide (20 mL) were added 7-methoxy-4-chloro-quinoline-6-carboxamide (0.983 g), 1-(2-chloro-4-hydroxyphenyl)-3-cyclopropylurea (1.13 g) and cesium carbonate (2.71 g), followed by heating and stirring at 70° C. for 23 hours. After the reaction mixture was allowed to cool down to room temperature, water (50 mL) was added, and the produced crystals were collected by filtration to give 1.56 g of the title compound (88% yield).

Workup

  1. temperatureby heating
  2. temperatureto cool down to room temperature
  3. filtrationthe produced crystals were collected by filtration

Sources & evidence

ORD record
ord-6353beaeb76347d78e7a374d651d132e
Source dataset
uspto-grants-2011_11
Patent number
US08058474B2

Reaction notes

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