6-(Piperidin-1-yl)pyrazine-2-carboxylic acid → HCID 178522719, Verbindung

HRID 414455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414455
[N:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=O)[CH:10]=[N:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1>O1CCCC1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>[N:1]1([C:7]2[N:12]=[C:11]([C:13]([NH:16][C:17]3[NH:21][N:20]=[N:19][N:18]=3)=[O:15])[CH:10]=[N:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 2

HCID 12825406-(Piperidin-1-yl)pyrazine-2-carboxylic acidHCID 178509299HCID 178509299, Verbindung

Produkt 1

HCID 178522719HCID 178522719, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 62493Pivaloyl chlorideLösungsmittel

Versuchsvorschrift

To a suspension fo 1.28 g of 6-(1-piperidinyl) pyrazine-2-carboxylic acid in 18 ml of tetrahydrofuran, 0.95 ml of triethylamine and 0.84 ml of pivaloyl chloride were added dropwise successively at 0 ° C. under stirring. After stirring for 1 hour at 0 ° C., 0.58 g of 5-amino-1H-tetrazole was added to the mixture, and the reaction mixture was stirred for 30 minutes at room temperature, and then refluxed for 12 hours. The reaction mixture was evaporated, and water was added to the residue. The precipitate was collected by filtration, and recrystalized from a mixture of dimethylsulfoxide and methanol affording 0.55 g of the desired compound as yellow columns. The obtained crystal was consistent with that of (a).

Aufarbeitung

  1. additionwere added dropwise successively at 0 ° C.
  2. stirringAfter stirring for 1 hour at 0 ° C.
  3. stirringthe reaction mixture was stirred for 30 minutes at room temperature
  4. temperaturerefluxed for 12 hours
  5. customThe reaction mixture was evaporated
  6. additionwater was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customrecrystalized from a mixture of dimethylsulfoxide and methanol affording 0.55 g of the desired compound as yellow columns

Quellen und Nachweise

ORD-Eintrag
ord-ae69f077e70c41669af0d3b2dac91c0e
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04792547

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