Stannous Chloride → N-(3-amino-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenyl)-4-chlorobenzamide

HRID 530774

Reaktionsgleichung

Reaktionsgleichung von HRID 530774
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[C:11]([N+:25]([O-])=O)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[Sn](Cl)Cl>CO>[NH2:25][C:11]1[CH:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:29][CH:28]=2)[CH:14]=[CH:13][C:12]=1[C:15]1[N:19]([CH3:20])[N:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 674670954-chloro-N-(4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3-nitrophenyl)benzamide

Produkt 1

HCID 67464229N-(3-amino-4-(1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)phenyl)-4-chlorobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Compound 16 (42 mg, 0.1 mmol) was dissolved in 10 ml MeOH. Tin(II)chloride dehydrate (223 mg, 1 mmol) was added and the reaction mixture was stirred at r.t. for overnight. The reaction mixture was evaporated to dryness. The solid residue was dissolved in 6 N NaOH and extracted with DCM. The org. phase was washed with brine. After concentrated to dryness, the solid residue was dissolved in DMF and purified on prep HPLC to give compound 17.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe solid residue was dissolved in 6 N NaOH
  3. extractionextracted with DCM
  4. washphase was washed with brine
  5. concentrationAfter concentrated to dryness
  6. dissolutionthe solid residue was dissolved in DMF
  7. custompurified on prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b040b2b233b145f481e1f95e6bcfc3d0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353099B2

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