1-(Furan-3-yl)methanamine → 4-[(3-Furylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 2217939

Reaktionsgleichung

Reaktionsgleichung von HRID 2217939
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[O:24]1[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25]1>CCO>[O:24]1[CH:28]=[CH:27][C:26]([CH2:29][NH:30][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:9][C:10]([F:12])([F:11])[F:13])[CH2:14][C:15]([F:18])([F:16])[F:17])=[O:7])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])=[CH:25]1

Komponenten

4

Edukt 2

HCID 27761971-(Furan-3-yl)methanamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Produkt 1

HCID 588744814-[(3-Furylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Following the general procedure for Intermediate 2 using 4-fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (103 mg, 0.296 mmol) and 3-furylmethylamine (35 mg, 0.355 mmol) in 3 mL of EtOH containing TEA (0.060 mL, 0.444 mmol). The product was purified by flash chromatography on silica gel using 3:1/hexanes:EtOAc as eluent. Yield: 114 mg (91%); 1H NMR (400 MHz, CHLOROFORM-D) δ 4.26 (q, J=8.40 Hz, 4H), 4.44 (d, J=5.27 Hz, 2H), 6.43 (m, 1H), 7.00 (d, J=8.98 Hz, 1H), 7.46 (m, 2H), 7.55 (dd, J=8.88, 2.05 Hz, 1H), 8.32 (d, J=2.15 Hz, 1H), 8.45 (m, 1H); MS (ESI) 425.72 (MH+).

Aufarbeitung

  1. customThe product was purified by flash chromatography on silica gel using 3:1/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-375133508ca0481791ce24d822ce5863
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407968B2

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