Urea → HCID 117664478, compound

HRID 2199495Notes

Reaction equation

HRID 2199495 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])=[C:10]([O:17][CH3:18])[CH:9]=[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:3]=1[C:4](OC)=[O:5].[NH2:27][C:28]([NH2:30])=[O:29]>C(O)C>[NH2:27][C:28]([NH:30][C:4](=[O:5])[C:3]1[C:8](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:9][C:10]([O:17][CH3:18])=[C:11]([CH2:12][CH2:13][C:14]([CH3:16])=[CH2:15])[C:2]=1[OH:1])=[O:29]

Participants

4

Reactant 2

HCID 1176UreaHCID 117664395HCID 117664395, compound

Product 1

HCID 117664478HCID 117664478, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve compound 8 (1.0 g, 2.96 mmol) in anhydrous ethanol (20 ml), add in urea (0.27 g, 4.44 mmol), reflux to react for 12h, after completion of the reaction, pour the solution into ice water and extract three times with ethyl acetate, pool the organic layer, dry over anhydrous magnesium sulfate, filter and concentrate the solution, feed the solution to a silica gel column, evaporate the solvent in the eluent to obtain a white solid as the desired product (0.89 g, 80%). 1H NMR (400 MHz, DMSO-d6): 1.79 (s, 3H), 1.82 (s, 3H), 3.34 (d, J=7.6 Hz, 2H), 3.83 (s, 3H), 5.21 (t, J=7.6 Hz, 1H), 6.20 (s, 2H), 6.65 (s, 1H), 6.81 (d, J=16.0 Hz, 1H), 7.26 (d, J=16.0 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 7.43 (d, J=7.6 Hz, 2H), 7.45 (t, J=7.6 Hz, 2H), 9.89 (s, 1H), 11.77 (s, 1H).

Workup

  1. temperaturereflux
  2. customafter completion of the reaction
  3. extractionextract three times with ethyl acetate, pool the organic layer
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate the solution
  7. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-2bd8fe9344a8496ca2c075d5555d1536
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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