Hydrochloric Acid → 6-ethyl-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indene

HRID 1478988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478988
C(OC([N:8]1[CH2:15][C:14]2[C:10](=[N:11][NH:12][C:13]=2[NH2:16])[CH2:9]1)=O)(C)(C)C.[CH2:17]([CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21])[CH3:18].Cl>CC(O)=O>[CH2:23]([C:19]1[C:20]([CH3:21])=[N:16][C:13]2[N:12]([N:11]=[C:10]3[CH2:9][NH:8][CH2:15][C:14]3=2)[C:17]=1[CH3:18])[CH3:24]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 737613-Ethylpentane-2,4-dioneHCID 178451527HCID 178451527, Verbindung

Produkt 1

HCID 896528476-ethyl-5,7-dimethyl-2,3-dihydro-1H-2,4,7a,8-tetraaza-cyclopenta[a]indeneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (0.6 g; 2.68 mmol; 1 eq.) and 3-ethyl-2,4-pentanedione (0.36 mL; 2.68 mmol; 1 eq.) in AcOH (8 mL) was stirred at room temperature for 32 hours. Aq. 32% HCl (1.05 mL; 10.7 mmol; 4 eq.) was added and the resulting mixture stirred for a further 16 hours. After concentration in vacuo, the residue was triturated in MTBE and the precipitate filtered off and dried. The solid was taken up in ethyl acetate and washed with 1M aq. NaOH (2×), dried over magnesium sulfate and concentrated in vacuo to afford the title compound (450 mg, 94%) as a beige solid. 1H NMR (DMSO-d6) δ 4.05-4.00 (m, 4H), 2.73-2.63 (m, 5H), 2.51 (s, 3H), 1.12 (t, J=7.4 Hz, 3H). UPLC/MS: (MS+) 217.3 ([M+H]+).

Aufarbeitung

  1. stirringthe resulting mixture stirred for a further 16 hours
  2. concentrationAfter concentration in vacuo
  3. customthe residue was triturated in MTBE
  4. filtrationthe precipitate filtered off
  5. customdried
  6. washwashed with 1M aq. NaOH (2×)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5fb68c0a50a04e44b9a566e7e028465b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403835B2

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