Dimethyl Sulfoxide → Lenvatinib

HRID 1670406Notes

Reaction equation

HRID 1670406 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-chloroquinoline-6-carboxamide (0.983 g), 1-(2-chloro-4-hydroxyphenyl)-3-cyclopropylurea (1.13 g) and cesium carbonate (2.71 g), and the mixture was stirred at 70° C. for 23 hours. The mixture was cooled to room temperature, addition of water (50 mL) yielded crystals, and the crystals were filtered off to give the title compound (1.56 g, yield 88%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customyielded crystals
  3. filtrationthe crystals were filtered off

Sources & evidence

ORD record
ord-36293c3d9767468da88ef9e60e0b470c
Source dataset
uspto-grants-2011_08
Patent number
US07994159B2

Reaction notes

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