Thionyl Chloride → HCID 23125712, compound

HRID 1820919Notes

Reaction equation

HRID 1820919 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O-:8])=O.S(Cl)(Cl)=O.[NH2:16][C:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:27].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:26]([C:18]2[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:17]=2[NH:16][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:10][CH3:11])=[O:9])=[O:27])=[N:30][CH:31]=1

Participants

8

Reactant 4

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 6994472Methyl adipateHCID 230625903-amino-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide

Product 1

HCID 23125712HCID 23125712, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Monomethyl adipate (2.55 g) is dissolved in chloroform (35 ml) and there to are added thionyl chloride (1.25 ml) and N,N-dimethylformamide (2 drops) at room temperature. The mixture is stirred at the same temperature for 3 hours and 20 minutes, and thereto are added 3-amino-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (3.50 g) obtained in Reference Example 80 and pyridine (5.0 ml). After stirring for 14.5 hours at room temperature, a saturated aqueous sodium hydrogen carbonate solution is added to the reaction solution, and the mixture is extracted with chloroform. The organic layer is washed with saturated brine, dried over sodium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diisopropyl ether and the precipitates are collected by filtration to give methyl 6-[(2-{[(5-chloropyridin-2-yl)amino]carbonyl}benzofuran-3-yl)amino]-6-oxohexanoate (4.72 g).

Workup

  1. stirringAfter stirring for 14.5 hours at room temperature
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure
  7. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-3699d46e38cb498fb5f84eeae86a3f2d
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Reaction notes

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