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5-hydrazinyl-1-methyl-1H-pyrazole → 4-(4-chlorophenyl)-5-(4-methoxybenzyl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873978
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873978
[C:1]([C:4]1[CH:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:6](=[O:25])[C:5]=1O)(=O)[CH3:2].[NH:27]([C:29]1[N:33]([CH3:34])[N:32]=[CH:31][CH:30]=1)[NH2:28]>CCO.C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:28][N:27]([C:29]4[N:33]([CH3:34])[N:32]=[CH:31][CH:30]=4)[C:5]=3[C:6](=[O:25])[N:7]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:10][CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 684257025-hydrazinyl-1-methyl-1H-pyrazoleHCID 1177028964-acetyl-5-(4-chlorophenyl)-3-hydroxy-1-[(4-methoxyphenyl)methyl]-2,5-dihydro-1H-pyrrol-2-one

Produkt 1

HCID 1177027824-(4-chlorophenyl)-5-(4-methoxybenzyl)-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-oneAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a stirred solution of 4-acetyl-5-(4-chlorophenyl)-3-hydroxy-1-(4-methoxybenzyl)-1H-pyrrol-2(5H)-one (Step 71.2) (3 g, 8.07 mmol) in EtOH (50 mL) and toluene (50 mL) was added 5-hydrazinyl-1-methyl-1H-pyrazole (Step 74.2) (1.941 g, 10.49 mmol) and the resulting mixture was heated up and stirred at 115° C. for 20 hr. The reaction was quenched with a saturated aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 40-50%) to afford the title product (3.15 g, 6.89 mmol, 85% yield) as yellow solid. tR: 5.60 min (HPLC 1); tR: 1.24 min (LC-MS 2); ESI-MS: 448 [M+H]+ (LC-MS 2); Rf=0.41 (hexane/EtOAc 1:1).

Aufarbeitung

  1. temperaturethe resulting mixture was heated up
  2. customThe reaction was quenched with a saturated aq. NaHCO3 solution
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel column chromatography (hexane/EtOAc 40-50%)

Quellen und Nachweise

ORD-Eintrag
ord-5880acb5d1534a64bed68a7a41bded1f
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975417B2

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