Sodium ethoxide → 6-Cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

HRID 730535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730535
CO[C:3]([C:5]1[N:6]([N:12]([C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:7]=[C:8]([C:10]#[N:11])[CH:9]=1)=[O:4].[O-]CC.[Na+]>C(O)C>[CH2:23]([O:22][C:20]([C:19]1[C:18](=[O:25])[N:12]([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[N:6]2[CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:5]2[C:3]=1[OH:4])=[O:21])[CH3:24]

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 687765484-cyano-1-[(2-ethoxycarbonyl-acetyl)-(3-methyl-butyl)-amino]-1H-pyrrole-2-carboxylic acid methyl ester

Produkt 1

HCID 598535636-Cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of crude 4-cyano-1-[(2-ethoxycarbonyl-acetyl)-(3-methyl-butyl)-amino]-1H-pyrrole-2-carboxylic acid methyl ester (Example 15d, 2.552 mmol) in ethanol (30 mL) was added a 21% solution of sodium ethoxide in ethanol (2.07 g, 6.380 mmol) and the mixture was heated at 40° C. for 16 h. Upon cooling, the mixture was quenched with 1.0 M aqueous hydrochloric acid solution and brine. The aqueous mixture was extracted with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude desired product, 6-cyano-4-hydroxy-1-(3-methyl-butyl)-2-oxo-1,2-dihydro-pyrrolo[1,2-b]pyridazine-3-carboxylic acid ethyl ester as a yellow solid, which was used in the next step without further purification. LC-MS (ESI) calcd for C16H19N3O4 317.14, found 318.3 [M+H+]. FT-IR (ATR) νmax (neat): 2231, 1642, 1610 cm−1.

Aufarbeitung

  1. temperatureUpon cooling
  2. customthe mixture was quenched with 1.0 M aqueous hydrochloric acid solution and brine
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-74fa406ba4824e7ebc8185db07596582
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582754B2

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