Carbon Dioxide → 6a,7,8,9-tetrahydro-6H-pyrido[3,2-e]pyrrolo[1,2-a][1,4]diazepine-6,11(5H)-dione

HRID 223337

Reaktionsgleichung

Reaktionsgleichung von HRID 223337
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)=O.C(N(CC)CC)C.[NH:21]1[CH2:29][CH2:28][CH2:27][C@H:22]1[C:23](OC)=[O:24]>O.CN(C)C=O>[N:4]1[C:3]2[C:8](=[O:10])[N:21]3[CH2:29][CH2:28][CH2:27][CH:22]3[C:23](=[O:24])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 738363-Aminopicolinic acidHCID 853477Methyl L-prolinate

Produkt 1

HCID 136881496a,7,8,9-tetrahydro-6H-pyrido[3,2-e]pyrrolo[1,2-a][1,4]diazepine-6,11(5H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

36 g (0.26 mol) of 3-aminopyridine-2-carboxylic acid, 46.6 g (0.29 mol) of N,N'-carbonyldiimidazole and 200 ml of dimethylformamide are stirred at room temperature until the carbon dioxide evolution has finished, then the mixture is treated with 26.3 g (0.26 mol) of triethylamine and 43.1 g (0.26 mol) of methyl L-prolinate and stirred at room temperature for a further 1.5 hours. Subsequently, the solution is poured into water, extracted four times with chloroform, the combined chloroform extracts are dried over magnesium sulphate and then evaporated in vacuo. The oily residue is treated with 500 ml of glacial acetic acid, heated to boiling under reflux for 1 hour and then evaporated to dryness. By recrystallization from ethanol there is obtained 6a,7,8,9-tetrahydro-6H-pyrido[3,2-e]pyrrolo[1,2-a][1,4]diazepine-6,11(5H)-dione of melting point 249°-250°.

Aufarbeitung

  1. extractionextracted four times with chloroform
  2. dry with materialthe combined chloroform extracts are dried over magnesium sulphate
  3. customevaporated in vacuo
  4. additionThe oily residue is treated with 500 ml of glacial acetic acid
  5. temperatureheated
  6. temperatureunder reflux for 1 hour
  7. customevaporated to dryness
  8. customBy recrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-dae290049fff4d6d93c619eeb9cd8eb3
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04353827

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