Hydrochloric Acid → HCID 23125711, compound

HRID 1820917

Reaction equation

HRID 1820917 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([O-:7])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][C:17]=1[C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][N:29]=1)=[O:26].Cl>C(Cl)(Cl)Cl.CN(C)C=O.N1C=CC=CC=1>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([NH:27][C:25]([C:17]2[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:16]=2[NH:15][C:5](=[O:7])[CH2:4][CH2:3][CH2:2][C:1]([O:9][CH3:10])=[O:8])=[O:26])=[N:29][CH:30]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 69931945-Methoxy-5-oxopentanoateHCID 23062590HCID 23062590, compound

Product 1

HCID 23125711HCID 23125711, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

Monomethyl glutarate (3.32 g) is dissolved in chloroform (50 ml) and thereto are added thionyl chloride (1.75 ml) and N,N-dimethylformamide (one drop). After stirring for 1.5 hours at the same temperature, the reaction solution is cooled, and thereto are added 3-amino-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (5.00 g) obtained in Reference Example 80 and pyridine (7.0 ml). After stirring for 2.5 hours at room temperature, the reaction solution is poured into 5% hydrochloric acid and extracted with chloroform. The organic layer is washed successively with saturated brine, a saturated aqueous sodium hydrogen carbonate solution and 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 5-[(2-{[(5-chloropyridin-2-yl)amino]carbonyl}benzofuran-3-yl)amino]-5-oxopentanoate (6.16 g). APCI-MS M/Z:416/418[M+H]+

Workup

  1. temperaturethe reaction solution is cooled
  2. stirringAfter stirring for 2.5 hours at room temperature
  3. extractionextracted with chloroform
  4. washThe organic layer is washed successively with saturated brine
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure
  8. filtrationthe precipitates are collected by filtration

Sources & evidence

ORD record
ord-c3542a4506fc4137b0d2af184aa3883b
Source dataset
uspto-grants-2009_10
Patent number
US07605158B2

Linked notes

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