Acetic Acid → HCID 89649623, Verbindung

HRID 2207597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2207597
C1(S([CH:10]2[CH:20]([C:21]3[CH:26]=[C:25]([Br:27])[CH:24]=[C:23]([CH3:28])[N:22]=3)[NH:19][C:12]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[CH2:11]2)(=O)=O)C=CC=CC=1.CC(C)([O-])C.[K+].C(O)(=O)C>C1COCC1>[Br:27][C:25]1[CH:24]=[C:23]([CH3:28])[N:22]=[C:21]([C:20]2[CH2:10][CH2:11][C:12]3([CH2:16][CH2:15][N:14]([CH3:17])[C:13]3=[O:18])[N:19]=2)[CH:26]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 23665647Potassium tert-butoxideHCID 89649142HCID 89649142, Verbindung

Produkt 1

HCID 89649623HCID 89649623, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 7-(benzenesulfonyl)-8-(4-bromo-6-methyl-2-pyridyl)-3-methyl-3,9-diazaspiro[4.4]nonan-4-one (which may be prepared as described in Description 12) in THF (20 mL) at 00° C. was added 1.7 M potassium tert-butoxide in THF (2.69 mL, 4.58 mmol) dropwise over 5 minutes. The reaction mixture was stirred at 00° C. for 1.5 hours. The reaction was quenched by the addition of acetic acid (0.26 mL, 4.58 mmol) and then the mixture was filtered, washed with dichloromethane and the filtrate concentrated at reduced pressure to give a brown gum. The product was purified by silica gel chromatography eluting with 40-100% ethyl acetate in iso-hexane to give racemic 2-(4-bromo-6-methyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one a pale yellow solid (D13) (314 mg);

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washwashed with dichloromethane
  3. concentrationthe filtrate concentrated at reduced pressure
  4. customto give a brown gum
  5. customThe product was purified by silica gel chromatography
  6. washeluting with 40-100% ethyl acetate in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ca396bb344d5432e8e0f1c8dffcbf468
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376436B2

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