Dimethylformamide → HCID 57765366, compound

HRID 2243051Notes

Reaction equation

C[N:2]([CH3:20])/[CH:3]=[C:4](/[C:10](=[O:19])[C:11]1[CH:16]=[C:15]([I:17])[CH:14]=[CH:13][C:12]=1F)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:21](N)[CH2:22][CH2:23]C.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(O)C.O>[CH2:20]([N:2]1[C:12]2[C:11](=[CH:16][C:15]([I:17])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3]1)[CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

A suspension of (Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (WO2006/010733, 415 mg, 1.06 mmol) in ethanol (6 mL) at room temperature was treated with N-butylamine (0.115 mL, 1.17 mmol). The reaction mixture was stirred until a yellow solution resulted, then concentrated under reduced pressure after 1 h. Potassium carbonate (220 mg, 1.59 mmol) and DMF (4 mL) were added to the concentrate, and the reaction mixture was heated to 70° C. for 3 h, cooled to room temperature, and allowed to stand overnight. The next day the reaction mixture was poured into water, and the solid that formed was collected by filtration, washed with water, dissolved in methylene chloride and concentrated under reduced pressure to give title compound which was placed on high vac to remove residual solvent. MS (ESP): 400 (M+H+) for C16H18INO3; NMR: 0.90 (t, J=7 Hz, 3H), 1.28 (t, J=6 Hz, 3H), 1.33 (m, 2H), 1.71 (m, 2H), 4.22 (q, J=7 Hz, 2H), 4.35 (m, 2H), 7.64 (m, 1H), 8.05 (m, 1H), 8.50 (m, 1H), 8.70 (s, 1H).

Workup

customresulted
concentrationconcentrated under reduced pressure after 1 h
temperaturecooled to room temperature
customthe solid that formed
filtrationwas collected by filtration
washwashed with water
dissolutiondissolved in methylene chloride
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-02396fd63212445481527d32d90480ac
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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