Hydrochloric Acid → Dimethyl 2-methyl-1-(tosylamino)-5-(3-methyl-2-pyrazinyl)pyrrole-3,4-dicarboxylate

HRID 1721819Notes

Reaction equation

HRID 1721819 reaction equation
[Na].[CH3:2][C:3]1[C:4]([C:9](=O)[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:5][CH:6]=[CH:7][N:8]=1.Cl[CH:17]([C:22](=[N:24][NH:25][S:26]([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH3:23])[C:18]([O:20][CH3:21])=[O:19].Cl>CO.C1COCC1>[CH3:23][C:22]1[N:24]([NH:25][S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:33])=[CH:34][CH:35]=2)(=[O:27])=[O:28])[C:9]([C:4]2[C:3]([CH3:2])=[N:8][CH:7]=[CH:6][N:5]=2)=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 20029397Methyl 3-(3-methylpyrazin-2-yl)-3-oxopropanoateHCID 73675184Methyl 2-chloro-3-(tosylhydrazono)butanoate

Product 1

HCID 20029390Dimethyl 2-methyl-1-(tosylamino)-5-(3-methyl-2-pyrazinyl)pyrrole-3,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

0.81 g of sodium was heated with 20 ml of methanol, then a solution of 6.8 g of 31A in 20 ml of methanol was added and the mixture was stirred at room temperature for 1 hour. Then a solution of 11.2 g of 7B in 25 ml of THF was added, and the mixture was stirred at room temperature for 2 hours. The mixture was stripped of volatiles, 100 ml of methanol was added to the residue and hydrogen chloride gas was bubbled through the mixture, which then was heated at reflux for 2 hours. The mixture was cooled, neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with methylene chloride. The extract was stripped of volatiles, and the residue was triturated with 10 ml of ether. The solid product was collected and dried (Na2SO4) to give dimethyl 2-methyl-1-(tosylamino)-5-(3-methyl-2-pyrazinyl)pyrrole-3,4-dicarboxylate (31C), as a light yellow solid, m.p.: 177°-178° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customwas bubbled through the mixture, which
  3. temperaturethen was heated
  4. temperatureat reflux for 2 hours
  5. temperatureThe mixture was cooled
  6. extractionextracted with methylene chloride
  7. customthe residue was triturated with 10 ml of ether
  8. customThe solid product was collected
  9. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-ca8b094aa9b142dbaa62e2d98cac24c2
Source dataset
uspto-grants-1989_08
Patent number
US04853027

Reaction notes

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