Hydrochloric Acid → HCID 25121370, compound

HRID 2189158Notes

Reaction equation

HRID 2189158 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.Cl.[NH2:26][C:27]([NH2:29])=[O:28]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])[NH:29][C:27](=[O:28])[N:26]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1176Urea2×HCID 59363788HCID 59363788, compound

Product 1

HCID 25121370HCID 25121370, compoundYield 34%

Conditions

Temperature
120 °C

Procedure

To a sealed pressure vessel were added (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-isobutoxyphenyl)prop-2-en-1-one (256 mg, 0.8 mmol), 4N HCl in dioxanes (5 mL), and urea (242 mg, 4 mmol). The pressure vessel was sealed and heated to 120° C. for 20 h. Another 200 mg of urea were added and heated for another 5 h. The reaction was then cooled to room temperature, concentrated under reduced pressure and the product was purified by preparative HPLC to result in 10 mg (34%) of the title compound. 1H-NMR (400 MHz, d6-DMSO): δ 7.74 (d, 1H), 7.67 (d, 1H), 7.63 (d, 1H), 7.50 (m, 1H), 7.18 (d, 2H), 7.05-7.10 (m, 2H), 3.85 (dd, 2H), 2.02 (m, 1H), 0.95 (d, 6H). MS (EI) for C21H20N2O4: 364 (MH+).

Workup

  1. customThe pressure vessel was sealed
  2. temperatureheated for another 5 h
  3. temperatureThe reaction was then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customthe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cd0eef1193ce4d84bdc6b2540a2b40f7
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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