Tetrahydrofuran → HCID 69311621, Verbindung

HRID 860448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860448
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[N:11]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:12]=[C:13]([CH2:20][C:21]([O:23]CC)=[O:22])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1)#[N:2].O1CCCC1.[OH-].[K+]>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]3[N:11]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:12]=[C:13]([CH2:20][C:21]([OH:23])=[O:22])[C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:8]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14797Potassium Hydroxide2×HCID 69308255HCID 69308255, Verbindung

Produkt 1

HCID 69311621HCID 69311621, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(4-cyanophenyl)-2-(2-ethoxy-2-oxoethyl)-7-ethylpyrrolo[1,2-b]pyridazine-3-carboxylate (77.9 mg) in ethanol (0.5 mL)-tetrahydrofuran (0.5 mL) was added 1N potassium hydroxide. The resulting solution was stirred for 25 hours at room temperature. The mixture was stirred for futher 1 hour after adding 1N potassium hydroxide (0.04 mL). The reaction was quenched by adding 1N hydrochloric acid (0.23 mL). The volatile was evaporated off, and the resulting residue was partitioned between ethyl acetate (10 mL) and 1N hydrochloric acid (6 mL). The organic layer was washed with brine, dried, and evaporated to give [4-(4-cyanophenyl)-3-(ethoxycarbonyl)-7-ethylpyrrolo[1,2-b]pyridazin-2-yl]acetic acid as an yellow solid (67.7 mg, 93.4%).

Aufarbeitung

  1. stirringThe mixture was stirred for futher 1 hour
  2. customThe reaction was quenched
  3. additionby adding 1N hydrochloric acid (0.23 mL)
  4. customThe volatile was evaporated off
  5. customthe resulting residue was partitioned between ethyl acetate (10 mL) and 1N hydrochloric acid (6 mL)
  6. washThe organic layer was washed with brine
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dbfc69dbf22f405abbad21d2a83201ff
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153854B2

Notizen zur Reaktion

Wird geladen…