N-ethyl-4-fluorobenzamide → HCID 66716928, compound

HRID 1184510Notes

Reaction equation

[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[CH3:13][CH:14]1[O:19][C:18]2[CH:20]=[CH:21][C:22]([O:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:23][C:17]=2[NH:16][C:15]1=[O:31]>>[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:28]2[CH2:29][CH2:30][CH:25]([O:24][C:22]3[CH:21]=[CH:20][C:18]4[O:19][CH:14]([CH3:13])[C:15](=[O:31])[NH:16][C:17]=4[CH:23]=3)[CH2:26][CH2:27]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

Reactant 2

HCID 4693101N-ethyl-4-fluorobenzamide

HCID 66716991HCID 66716991, compound

Product 1

HCID 66716928HCID 66716928, compoundYield 6%

Procedure

Using N-ethyl-4-fluorobenzamide 281 as the alkylating agent, the reaction with 394E was carried out as described for 395 providing the title compound as a tan solid (0.0051 g, 6.0% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3H) 1.40 (d, J=6.57 Hz, 3H) 1.59-1.74 (m, 2H) 1.92-2.07 (m, 1H) 3.08-3.34 (m, 3H) 3.54-3.69 (m, 2H) 4.36-4.50 (m, 1H) 4.58 (q, J=6.65 Hz, 1H) 6.50 (d, J=2.78 Hz, 1H) 6.52-6.63 (m, 1H) 6.88 (d, J=8.59 Hz, 1H) 6.92-7.04 (m, 2H) 7.72 (d, J=8.84 Hz, 2H) 8.18 (s, 1 H) 10.56 (s, 1H). ESI-MS: m/z 410.3 (M+H)+.

Sources & evidence

ORD record: ord-84aeb77123d048f3a32b464fdebe20f5
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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