1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58674703, compound

HRID 1994159Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)/[CH:6]=[C:7](\[CH2:11][CH3:12])/[C:8]([OH:10])=O.[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:8](=[O:10])/[C:7](=[CH:6]/[C:5]2[CH:13]=[CH:14][CH:15]=[C:3]([O:2][CH3:1])[CH:4]=2)/[CH2:11][CH3:12])=[CH:19][C:18]=1[C:24]([F:25])([F:26])[F:27]

Participants

Conditions

Temperature: 0 °C

Procedure

(2E)-2-(3-methoxybenzylidene)butanoic acid (190 mg, 0.92 mmol), 4-chloro-3-(trifluoromethyl)aniline (189 mg, 0.97 mmol) and DMAP (135 mg, 1.11 mmol) were mixed together and stirred in DCM (15 mL). The reaction mixture was cooled to 0° C. and EDCI (118 mg, 1.29 mmol) was added. The reaction was allowed to warm slowly to rt overnight. The mixture was diluted with DCM and washed with 1N HCl, sat. NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (SiO2, 0-15% EtOAc in hexanes) to give the title compound (216 mg). 1H NMR (400 MHz, d6-DMSO): δ 10.44 (s, 1H), 8.29 (d, 1H), 8.05-8.02 (dd, 1H), 7.68 (d, 1H), 7.39-7.35 (m, 1H), 7.22 (s, 1H), 6.99 (d, 1H), 6.95-6.93 (m, 2H), 3.77 (s, 3H), 2.54 (q, 2H), and 1.08 (t, 3H).

Workup

temperatureto warm slowly to rt overnight
washwashed with 1N HCl, sat. NaHCO3 and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (SiO2, 0-15% EtOAc in hexanes)

Sources & evidence

ORD record: ord-1cc91cb58da44061bd9e61c3855ed956
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652041B2

Reaction notes

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