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Hydrazine, cyclopropyl-, hydrochloride (1:1) → 4-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-one

HRID 873951
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 873951
[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]([C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)[C:6](=[O:27])[C:5]=1O)(=O)[CH3:2].Cl.[CH:30]1([NH:33][NH2:34])[CH2:32][CH2:31]1>CCO.C1(C)C=CC=CC=1>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([CH:8]2[C:4]3[C:1]([CH3:2])=[N:34][N:33]([CH:30]4[CH2:32][CH2:31]4)[C:5]=3[C:6](=[O:27])[N:7]2[C:16]2[CH:17]=[C:18]([CH3:26])[C:19]3[N:20]([C:22]([CH3:25])=[N:23][N:24]=3)[CH:21]=2)=[CH:14][CH:13]=1
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Komponenten

5

Edukt 2

HCID 19594967Hydrazine, cyclopropyl-, hydrochloride (1:1)HCID 1177026714-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one

Produkt 1

HCID 862933504-(4-chlorophenyl)-1-cyclopropyl-5-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-methyl-4,5-dihydropyrrolo-[3,4-c]pyrazol-6(1H)-oneAusbeute 59,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-acetyl-5-(4-chlorophenyl)-1-(3,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-hydroxy-1H-pyrrol-2(5H)-one (Step 92.1) (630 mg, 1.588 mmol) and cyclopropylhydrazine hydrochloride (517 mg, 4.76 mmol) in EtOH (8 mL) and toluene (8 mL) was stirred for 2 hr at reflux. The reaction mixture was concentrated, diluted with CH2Cl2/saturated aq. NaHCO3 solution, and extracted with CH2Cl2. The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated. The crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2) to afford the title product (412 mg, 0.952 mmol, 59.9% yield) as a yellow foam. tR: 0.95 min (LC-MS 2); ESI-MS: 433 [M+H]+ (LC-MS 2); Rf=0.28 (1% ammonia/5% MeOH/CH2Cl2); 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98-1.11 (m, 2H) 1.18-1.29 (m, 2H) 1.92 (s, 3H) 2.43 (s, 3H) 2.61 (s, 3H) 3.75-3.87 (m, 1H) 6.41 (s, 1H) 7.27-7.39 (m, 5H) 8.33-8.48 (m, 1H).

Aufarbeitung

  1. temperatureat reflux
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with CH2Cl2/saturated aq. NaHCO3 solution
  4. extractionextracted with CH2Cl2
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude material was purified by silica gel column chromatography (1% ammonia/5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-65cd1ee6f6d646d39835dec548bcd0dc
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975417B2

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