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

HRID 1721819ノート

反応式

HRID 1721819 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ca8b094aa9b142dbaa62e2d98cac24c2
出典データセット
uspto-grants-1989_08
特許番号
US04853027

反応ノート

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