Acetonitrile → HCID 11281937, compound

HRID 130672Notes

Reaction equation

HRID 130672 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:26]=[CH:25][C:16]4[C:17]([C:21]([NH:23][CH3:24])=[O:22])=[C:18]([CH3:20])[O:19][C:15]=4[CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:28][CH2:29][CH2:30][C:31]([O:33]C)=[O:32].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>CN(C=O)C>[CH3:20][C:18]1[O:19][C:15]2[CH:14]=[C:13]([O:12][C:6]3[C:5]4[C:10](=[CH:11][C:2]([O:1][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)[CH:26]=[CH:25][C:16]=2[C:17]=1[C:21]([NH:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 107604Methyl 4-bromobutyrateHCID 135507449HCID 135507449, compound

Product 1

HCID 11281937HCID 11281937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-[(7-hydroxyquinolin-4-yl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide 119-A (200mg, 0.57 mmol), methyl 4-bromobutanoate (155mg, 0.85 mmol), and Cs2CO3 (433 mg, 1.14 mmol) in a mixed solvent of CH3CN (4 mL)/DMF(1 mL) was heated to 65° C. overnight. The reaction mixture was extracted with EtOAc, concentrated and dissolved in 5 mL of MeOH. To the solution was added 1 N NaOH (1 mL). The solution was stirred at room temperature for 2 hours and then heated to 60° C. for 2 hours. The solution was acidified with AcOH to a pH of about 6 and extracted with EtOAc. The concentrated residue was purified by HPLC using 20-60% CH3CN/H2O over 30 min. to give 4-{[4-({2-methyl-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}oxy)quinolin-7-yl]oxy}butanoic acid 119.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. concentrationconcentrated
  3. dissolutiondissolved in 5 mL of MeOH
  4. additionTo the solution was added 1 N NaOH (1 mL)
  5. temperatureheated to 60° C. for 2 hours
  6. extractionextracted with EtOAc
  7. customThe concentrated residue was purified by HPLC
  8. customover 30 min.

Sources & evidence

ORD record
ord-94f2e8842e89497f9e19db36a4080639
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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