Methanol → Tert-butyl 3-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1-carboxylate

HRID 1035267

Reaktionsgleichung

Reaktionsgleichung von HRID 1035267
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[CH2:10][CH:11]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][N:12]1C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O.N1CCNCC1.CO>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:41])[CH2:10][CH:11]1[NH:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:16]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4837PiperazineHCID 582849301-(9H-fluoren-9-yl)methyl 4-tert-butyl 2-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1,4-dicarboxylate

Produkt 1

HCID 58284918Tert-butyl 3-(2-(2-bromophenylamino)-2-oxoethyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 1A (8.76 g, 14.12 mmol) in dichloromethane (100 mL) was added piperazine (3.65 g, 42.4 mmol). Methanol (50 mL) was added to the solution for solubility, and the resultant mixture was warmed to 40° C. for 14 hours. Once the reaction was complete, purification via flash chromatography (20-100% ethyl acetate/hexanes) afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 10.34 (s, 1H), 7.83 (d, J=7.12 Hz, 1H), 7.64 (dd, J=7.97, 1.53 Hz, 1H), 7.35 (dd, 1H), 7.08 (dd, 1H), 3.69-3.85 (m, 2H), 2.70-2.99 (m, 3H), 2.53-2.67 (m, 2H), 2.42 (d, J=6.44 Hz, 2H), 1.34-1.46 (m, 9H); MS (APCI+) m/z 400.0 (M+H)+.

Aufarbeitung

  1. custompurification via flash chromatography (20-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9b82d599d6c446f58f7e6f34ef1d64ca
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546377B2

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