Cesium carbonate → HCID 67299224, compound

HRID 2068221Notes

Reaction equation

HRID 2068221 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1([OH:12])[CH2:11][CH2:10]1)(=O)=O.O[C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:32]([C:34]4([C:37]([NH2:39])=[O:38])[CH2:36][CH2:35]4)=[O:33])=[CH:27][C:26]=3[F:46])=[CH:19][CH:20]=[N:21]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[OH:12][C:9]1([CH2:8][CH2:7][CH2:6][O:5][C:14]2[CH:23]=[C:22]3[C:17]([C:18]([O:24][C:25]4[CH:30]=[CH:29][C:28]([N:31]([C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=5)[C:32]([C:34]5([C:37]([NH2:39])=[O:38])[CH2:35][CH2:36]5)=[O:33])=[CH:27][C:26]=4[F:46])=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86640796HCID 86640796, compoundHCID 136347992N-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-N-phenylcyclopropane-1,1-dicarboxamide

Product 1

HCID 67299224HCID 67299224, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of 3-(1-hydroxycyclopropyl)propyl methanesulfonate (170.7 mg, 0.877 mmol, from example 9) and N-(4-(7-hydroxyquinolin-4-yloxy)-3-fluorophenyl)-N-phenylcyclopropane-1,1-dicarboxamide (300 mg, 0.656 mmol) in 5 mL of N,N-dimethylacetamide was added cesium carbonate (893 mg, 2.74 mmol). After stirring at room temperature for 36 hrs, then the reaction mixture was warmed to 40° C. for 8 hrs. The reaction mixture was concentrated in vacuo and the residue was chromatographed with a silica gel column (4:1 (v/v) EtOAc/n-hexane) to afford the title compound as a white solid (364.1 mg, 74%).

Workup

  1. temperaturethe reaction mixture was warmed to 40° C. for 8 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was chromatographed with a silica gel column (4:1 (v/v) EtOAc/n-hexane)

Sources & evidence

ORD record
ord-b41a2905574843d2997ced203e55b76f
Source dataset
uspto-grants-2012_10
Patent number
US08293897B2

Reaction notes

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