Ammonium Chloride → tert-butyl (+/-)-4-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-2-methylpiperazine-1-carboxylate

HRID 1915896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1915896
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]2[N:12]([CH2:13][C:14]([F:17])([F:16])[F:15])[N:11]=[CH:10][C:9]=2[N+:18]([O-])=O)[CH2:5][CH2:4][N:3]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[NH4+].[Cl-]>CO.O.[Zn]>[NH2:18][C:9]1[CH:10]=[N:11][N:12]([CH2:13][C:14]([F:16])([F:17])[F:15])[C:8]=1[N:6]1[CH2:5][CH2:4][N:3]([C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[CH:2]([CH3:1])[CH2:7]1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 86680103(+/-) tert-butyl 2-methyl-4-(4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)piperazine-1-carboxylate

Produkt 1

HCID 86680104tert-butyl (+/-)-4-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-2-methylpiperazine-1-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of (±) tert-butyl 2-methyl-4-(4-nitro-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)piperazine-1-carboxylate (370 mg, 0.94 mmol) in MeOH (15 mL) and H2O (3 mL) was added zinc (362 mg, 5.6 mmol) and NH4Cl (400 mg, 7.5 mmol). The reaction mixture was stirred at ambient temperature for 4 hours, filtered through Celite, and evaporated under reduced pressure to afford tert-butyl (±)-4-(4-amino-1-(2,2,2-trifluoroethyl)-1H-pyrazol-5-yl)-2-methylpiperazine-1-carboxylate as yellow solid (300 mg, 88%). MS (ESI) m/z: 364 [M+H+].

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2af3301459c04334b1a2afaa69365502
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614206B2

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