N-(2-aminoethyl)acetamide → 4-{[2-(acetylamino)ethyl]amino}-N,N-diethyl-3-nitrobenzamide

HRID 1796453Notes

Reaction equation

[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[NH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23]>CCO>[C:22]([NH:21][CH2:20][CH2:19][NH:18][C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:16][CH3:17])[CH2:1][CH3:2])=[O:15])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13])(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 90 °C

Procedure

Following general procedure 2B: A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (0.200 g, 0.833 mmol), N-(2-aminoethyl)acetamide (0.077 g, 0.757 mmol) in 80% aq. EtOH (5 mL) was heated at 90° C. overnight. After work-up, the crude product was purified by silica gel column chromatography (100% EtOAc to 5% MeOH/EtOAc) to provide the title compound (0.152 g, 63%) as a bright yellow solid. 1H-NMR (CDCl3): δ 8.27 (d overlapping with br s, J=2.0 Hz, 2H), 7.55 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 6.99 (d, J=9.2 Hz, 1H), 6.06 (br s, 1H), 3.58–3.50 (m, 4H), 3.44 (br s, 4H), 2.02 (s, 3H), 1.22 (t, J=7.2 Hz, 6H). MS (ESI) (M+H)+=323.

Workup

customAfter work-up, the crude product was purified by silica gel column chromatography (100% EtOAc to 5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-1ba8569fe2ba49c0bf05eb58a3ede7ed
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030139B2

Reaction notes

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