Toluene → 4-(3-(4-bromo-2,3-difluorophenyl)ureido)-N,N-dimethyl-benzamide

HRID 517433Notes

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[C:3]=1[F:10].ClC(Cl)(Cl)C[O:14][C:15](=O)[NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:27])[N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15](=[O:14])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:24]([CH3:26])[CH3:25])=[O:27])=[CH:19][CH:18]=2)=[C:4]([F:9])[C:3]=1[F:10]

Participants

Conditions

Temperature: 105 °C

Procedure

To a 50 mL round bottom flask, 4-bromo-2,3-difluoroaniline (0.5 g, 0.0024 mol), 2,2,2-trichloroethyl(4-(dimethylcarbamoyl)phenyl)carbamate (0.978 g, 0.00288 mol; from Preparation 5), TEA (1.01 mL, 0.0072 mol) and toluene (20 mL) were added. The reaction mixture was maintained at 105° C. for 12 h. The cooled reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to get the crude product. The crude was purified by column chromatography using 3% MeOH in chloroform to get the title compound [0.35 g, 36%]. 1H NMR (300 MHz, DMSO-d6): δ 9.30 (s, 1H), 8.96 (s, 1H), 8.0-7.92 (m, 1H), 7.52-7.42 (m, 2H), 7.39 (d, J=8.4 Hz, 2H), 7.20-7.06 (m, 1H), 2.96 (s, 6H); LC-MS (ESI): Calculated mass: 397.0; Observed mass: 400.0 (RT: 1.49 min).

Workup

customThe cooled reaction mixture
washwashed with water
dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customto get the crude product
customThe crude was purified by column chromatography

Sources & evidence

ORD record: ord-89c6b8883844430582cbd12b6811273c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115092B2

Reaction notes

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