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Ammonium Chloride → (S)-N3-(5-Cyclopropyl-1H-pyrazol-3-yl)-2,6-difluoro-N1-(1-(4-fluorophenyl)ethyl)benzene-1,3,4-triamine

HRID 1092251
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1092251
[Cl-].[NH4+].[CH:3]1([C:6]2[NH:10][N:9]=[C:8]([NH:11][C:12]3[C:17]([N+:18]([O-])=O)=[CH:16][C:15]([F:21])=[C:14]([NH:22][C@H:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[CH3:24])[C:13]=3[F:32])[CH:7]=2)[CH2:5][CH2:4]1.C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[CH:3]1([C:6]2[NH:10][N:9]=[C:8]([NH:11][C:12]3[C:13]([F:32])=[C:14]([NH:22][C@H:23]([C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[CH3:24])[C:15]([F:21])=[CH:16][C:17]=3[NH2:18])[CH:7]=2)[CH2:5][CH2:4]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 517165Ammonium AcetateHCID 86621771(S)-N-(5-Cyclopropyl-1H-pyrazol-3-yl)-2,4-difluoro-N3-(1-(4-fluorophenyl)ethyl)-6-nitrobenzene-1,3-diamine

Produkt 1

HCID 86621763(S)-N3-(5-Cyclopropyl-1H-pyrazol-3-yl)-2,6-difluoro-N1-(1-(4-fluorophenyl)ethyl)benzene-1,3,4-triamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994
Zinc
Katalysator
HCID 21899815MeOH tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of saturated ammonium chloride (4 ml) was added slowly to a suspension of (S)-N1-(5-cyclopropyl-1H-pyrazol-3-yl)-2,4-difluoro-N3-(1-(4-fluorophenyl)ethyl)-6-nitrobenzene-1,3-diamine (Method 102, 0.30 g, 0.719 mmol) and zinc dust (0.235 g, 3.59 mmol) in MeOH/THF (10 ml, 1:1). The mixture was stirred at 25° C. for 2 hours. Saturated ammonium acetate solution (5 ml) was added and the mixture was stirred for another 30 minutes. Zn dust was removed by filtration and the cake was washed with EtOAc (15 ml). The organic layer was separated and dried over sodium sulfate. After removal of solvent, the product was used directly for the next step without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred for another 30 minutes
  2. customZn dust was removed by filtration
  3. washthe cake was washed with EtOAc (15 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of solvent
  7. customthe product was used directly for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ec761648615b4b7ba149ed754d78928f
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08129403B2

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