Triethylamine → 8-{2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethylsulfonylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate

HRID 2259913Notes

Reaction equation

HRID 2259913 reaction equation
ClC[CH2:3][S:4](Cl)(=[O:6])=[O:5].[NH2:8][C:9]1[C:18]2[O:17][C:16](C3C=CC=CC=3)=C(C)C(=O)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH:27]([S:29]([NH:32][C:33]1[C:42]2[O:41][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[C:39]([CH3:49])[C:38](=[O:50])[C:37]=2[CH:36]=[CH:35][CH:34]=1)(=[O:31])=[O:30])=[CH2:28].[CH2:51]([N:53](CC)[CH2:54][CH3:55])[CH3:52]>>[CH3:3][S:4]([OH:6])(=[O:17])=[O:5].[CH3:16][O:17][C:18]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:8]1[CH2:55][CH2:54][N:53]([CH2:28][CH2:27][S:29]([NH:32][C:33]2[C:42]3[O:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[C:39]([CH3:49])[C:38](=[O:50])[C:37]=3[CH:36]=[CH:35][CH:34]=2)(=[O:31])=[O:30])[CH2:51][CH2:52]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 199728088-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyranHCID 199728168-(ethenylsulfonylamino)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Product 1

HCID 199725388-{2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethylsulfonylamino}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran methanesulfonate

Conditions

Temperature
0 °C

Procedure

1.05 ml of 2-chloroethanesulfonyl chloride was added dropwise to a solution of 5 g of 8-amino-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran and 1.4 ml of triethylamine stirred at 0° C. The reaction mixture was stirred at room temperature for 2 days. After filtering the precipitated solid, the solution was evaporated to dryness in vacuo to give a crude residue containing 8-(ethenylsulfonylamino)-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran used without further purification. A mixture of 7.54 g of this residue and 5.8 g of 1-(2-methoxyphenyl)piperazine and 4.15 g of potassium carbonate in 100 ml of dimethylformamide was stirred at room temperature for 4 hours, poured into 600 ml of water and extracted with ethyl acetate. The organic layer was evaporated to dryness in vacuo and the residue was purified by column chromatography on silica gel eluting with petroleum ether-acetone 8:2. The collected fractions were evaporated to dryness in vacuo and crystallized from 70% ethanol to give 0.75 g of the title compound as a base. This solid was dissolved in dichloromethane and 1 equivalent of methanesulfonic acid was added to the solution. The crude methanesulfonate, obtained by evaporation in vacuo, was crystallized from acetone, yielding 0.6 g of the title compound melting at 202°-203° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 days
  2. filtrationAfter filtering the precipitated solid
  3. customthe solution was evaporated to dryness in vacuo
  4. customto give a crude residue
  5. customused without further purification
  6. additionA mixture of 7.54 g of this residue and 5.8 g of 1-(2-methoxyphenyl)piperazine and 4.15 g of potassium carbonate in 100 ml of dimethylformamide
  7. stirringwas stirred at room temperature for 4 hours
  8. additionpoured into 600 ml of water
  9. extractionextracted with ethyl acetate
  10. customThe organic layer was evaporated to dryness in vacuo
  11. customthe residue was purified by column chromatography on silica gel eluting with petroleum ether-acetone 8:2
  12. customThe collected fractions were evaporated to dryness in vacuo
  13. customcrystallized from 70% ethanol

Sources & evidence

ORD record
ord-8a56984cb7964c428337f6c712b3bed3
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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