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Hydrochloric Acid → N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

HRID 2368472
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2368472
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]2[S:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.[CH3:36][N:37]1[CH:41]=[C:40]([CH2:42][NH:43][CH3:44])[C:39]([CH3:45])=[N:38]1.C(N(CC)CC)C.CCCP(=O)=O.Cl.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:36][N:37]1[CH:41]=[C:40]([CH2:42][N:43]([CH3:44])[C:13]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]([SH:16])=[N:10][CH:11]=2)=[O:15])[C:39]([CH3:45])=[N:38]1
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Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 70102001-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamineHCID 16167369Propylphosphoric anhydrideHCID 711174681-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acid

Produkt 1

HCID 178434002N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-(4-fluorophenyl)-2-(tritylthio)-1H-imidazole-5-carboxylic acid (6) (3.24 g, 6.74 mmol), 1-(1,3-dimethyl-1H-pyrazol-4-yl)-N-methylmethanamine (0.95 g, 6.80 mmol), triethylamine (5.70 mL, 40.9 mmol) and propylphosphonic anhydride (T-3-P)(50% in ethyl acetate, 4.85 mL, 8.15 mmol) in dichloromethane (50 mL) was stirred overnight at room temperature. To the reaction 6N HCl (10 mL) was carefully added and was stirred at room temperature for 40 minutes. The solution was basified with saturated sodium bicarbonate and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% MeOH in dichloromethane) to afford N-((1,3-dimethyl-1H-pyrazol-4-yl)methyl)-1-(4-fluorophenyl)-2-mercapto-N-methyl-1H-imidazole-5-carboxamide

Aufarbeitung

  1. additionwas carefully added
  2. extractionwas extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (0-20% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-3620f747981c4daa96246c81b3abe3f8
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08703776B2

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