Trifluoroacetic acid → HCID 67125813, Verbindung

HRID 2042409Notizen

Reaktionsgleichung

[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A stirred solution of tert-butyl 4-(7-methyl-furo[3,2-c]pyridin-4-yl)-piperazine-1-carboxylate (step A) (2.34 g, 7.37 mmol) in dichloromethane (4.1 ml) was cooled to 0° C., trifluoroacetic acid (8.41 g, 5.68 ml, 73.7 mmol) was added drop wise and the reaction mixture was allowed to stir for 10 min at 0° C. and for 30 min at room temperature. The solution was poured onto ice and 2N sodium carbonate solution (50 ml) and extracted with dichloromethane (2×25 ml). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1) to yield 7-methyl-4-(piperazin-1-yl)-furo[3,2-c]pyridine as a yellow solid (1.27 g, 79%), MS (ISP) m/z=218.4 [(M+H)+], mp 111.5° C.

Aufarbeitung

extractionextracted with dichloromethane (2×25 ml)
washThe combined organic layers were washed with brine (30 mL)
dry with materialdried (MgSO4)
customevaporated
customThe crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1)

Quellen und Nachweise

ORD-Eintrag: ord-05393eb23f4a4c91a84196bcd4a80fc5
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08586579B2

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