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Potassium Carbonate → HCID 24964085, Verbindung

HRID 655277
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 655277
Cl.Cl.[C:3]1([C:9]2[N:14]=[N:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][C:29](O)=O)[CH:24]=2)[N:19]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][C:29]3[N:13]4[N:14]=[C:9]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH:10]=[CH:11][C:12]4=[N:15][N:16]=3)[CH:24]=2)[N:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59320364HCID 59320364, VerbindungHCID 687055603-Hydrazino-6-phenylpyridazine dihydrochloride

Produkt 1

HCID 24964085
HCID 24964085, Verbindung
Ausbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A vial was charged with (6-phenyl-pyridazin-3-yl)-hydrazine dihydrochloride (20 mg, 0.077 mmol), (2-methyl-quinolin-6-yl)-acetic acid (17 mg, 0.085 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (22 mg, 0.115 mmol), 1-hydroxybenzotriazole hydrate (11 mg, 0.077 mmol), potassium carbonate (32 mg, 0.231 mmol), and N,N-dimethyl formamide (0.7 mL). The reaction mixture was stirred at room temperature for 14 h. After such time the mixture was concentrated in vacuo. Acetic acid (1 mL) was added to the residue and the resulting reaction mixture was stirred at 55° C. for 5 h. After such time the mixture was concentrated in vacuo and partitioned between 1 M aqueous potassium carbonate and ethyl acetate. The organic layer was washed with 1 M aqueous potassium carbonate, then brine, and directly adsorbed on silica gel. Purification on silica gel with 0-8% gradient of methanol in ethyl acetate afforded the title compound (8.7 mg, 0.024 mmol, 32% yield) as a light yellow solid. Analytical data presented in Table 1.

Aufarbeitung

  1. concentrationAfter such time the mixture was concentrated in vacuo
  2. additionAcetic acid (1 mL) was added to the residue
  3. customthe resulting reaction mixture
  4. stirringwas stirred at 55° C. for 5 h
  5. concentrationAfter such time the mixture was concentrated in vacuo
  6. custompartitioned between 1 M aqueous potassium carbonate and ethyl acetate
  7. washThe organic layer was washed with 1 M aqueous potassium carbonate
  8. customPurification on silica gel with 0-8% gradient of methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0c51c7547dd748938aea0bd0ba7eb37c
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071581B2

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