Hydrochloric Acid → Methyl 5-({2-amino-5-[(4-methyl-1-piperazinyl)methyl]phenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate

HRID 883576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883576
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N+:38]([O-])=O)=[C:13]([NH:15][C:16]3[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([O:25][C@@H:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[CH3:27])[CH:17]=3)[CH:14]=2)[CH2:4][CH2:3]1.Cl.COC(OC)OC>C1(C)C=CC=CC=1.[Pd]>[NH2:38][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:14][C:13]=1[NH:15][C:16]1[S:20][C:19]([C:21]([O:23][CH3:24])=[O:22])=[C:18]([O:25][C@@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]([F:35])([F:37])[F:36])[CH3:27])[CH:17]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 9005Trimethyl orthoformateHCID 44185548(R)-Methyl 5-((5-((4-methylpiperazin-1-yl)methyl)-2-nitrophenyl)amino)-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate

Produkt 1

HCID 57538942Methyl 5-({2-amino-5-[(4-methyl-1-piperazinyl)methyl]phenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of methyl 5-({5-[(4-methyl-1-piperazinyl)methyl]-2-nitrophenyl}amino)-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate (0.24 g, 0.415 mmol), 5% Pd/C (0.144 g), HCl (1.25 M in MeOH, 0.034 mL, 0.043 mmol), trimethylorthoformate (1.66 mL, 15.2 mmol) in toluene (0.58 mL) was hydrogenated under a H2 atmosphere at 1.1 bar pressure overnight. The vessel was purged with N2 and the reaction mixture was analysed by HPLC to confirm presence of the title compound which was not purified, but used crude in the next step. LRMS found m/z [ES+] 549.

Aufarbeitung

  1. customwas hydrogenated under a H2 atmosphere at 1.1 bar pressure overnight
  2. customThe vessel was purged with N2
  3. customwas not purified

Quellen und Nachweise

ORD-Eintrag
ord-8b5f1db41e784fa4804b6a06661a95ed
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236954B2

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