Pyridine → HCID 22909121, Verbindung

HRID 1379037Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1379037
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[C:11]3[NH:12][N:13]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:33](Cl)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[C:33]([N:12]1[C:11]2=[C:20]([C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]2[CH2:15][CH2:14][N:13]1[CH2:16][CH:17]([CH3:19])[CH3:18])(=[O:35])[CH3:34]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 136395922HCID 136395922, Verbindung

Produkt 1

HCID 22909121HCID 22909121, VerbindungAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel2×

Versuchsvorschrift

To a mixture of 7-(4-fluorophenyl)-2-isobutyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo[5,1-c][1,2,4]triazine (70 mg, 0.199 mmol) and pyridine (31 mg, 0.398 mmol) in N-methyl-2-pyrrolidone (1.2 ml) was added acetyl chloride (19 mg, 0.239 mmol) in N-methyl-2-pyrrolidone (0.3 ml) at ambient temperature. The reaction mixture was stirred for 1 hour, then aqueous saturated sodium bicarbonate and ethyl acetate were added thereto. The organic phase was separated, and washed with water, brine, and dried over sodium sulfate. The solvent was evaporated, and the obtained residue was purified by column chromatography on silica gel (eluent:dichloromethane/methanol; 100/1~40/1). The fractions containing the object compound were concentrated in vacuo and the obtained oil was crystallized from diisopropyl ether to give 1-acetyl-7-(4-fluorophenyl)-2-isobutyl-8-(pyridin-4-yl)-1,2,3,4-tetrahydropyrazolo-[5,1-c][1,2,4]triazine (57.0 mg).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent:dichloromethane/methanol; 100/1~40/1)
  6. additionThe fractions containing the object compound
  7. concentrationwere concentrated in vacuo
  8. customthe obtained oil was crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b61adf3b975142ba97adf9b5daf34dda
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670503

Notizen zur Reaktion

Wird geladen…