5-Amino-1,2,4-thiadiazole → N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide

HRID 390424

Reaktionsgleichung

Reaktionsgleichung von HRID 390424
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)[N:3]=1.[S:24]1[C:28]([NH2:29])=[N:27][CH:26]=[N:25]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[S:24]1[C:28]([NH:29][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][C:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=3)[N:3]=2)=[N:27][CH:26]=[N:25]1

Komponenten

5

Edukt 3

HCID 2902745-Amino-1,2,4-thiadiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59352891N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide

Produkt 1

HCID 59450317N-(4-(4-(1,2,4-thiadiazol-5-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Versuchsvorschrift

To a round bottom flask was added N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)-3,3,3-trifluoropropanamide (350 mg, 0.9 mmol), 1,2,4-thiadiazole-5-amine (100 mg, 0.9 mmol), xanthphos (50 mg, 0.1 mmol), Pd2 dba3 (50 mg, 0.05 mmol), NaCO3 (150 mg, 1.5 mmol) and dioxane(10 cm). The mixture was flushed with nitrogen and then brought to reflux for 2 hours. The mixture was filtered, partitioned between ethylacetate and bicarbonate. The organic layer was dried with magnesium sulfate, and concentrated to an oil, which was purified by column chromatography to yield the product as a yellow solid (127 mg, 34%)

Aufarbeitung

  1. customThe mixture was flushed with nitrogen
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. custompartitioned between ethylacetate and bicarbonate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated to an oil, which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b08aecb389014c2983dc64e972c5b12a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383633B2

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