Urea → HCID 59645413, compound

HRID 2253284Notes

Reaction equation

HRID 2253284 reaction equation
[O-]CC.[Na+].[NH2:5][C:6]([NH2:8])=[O:7].C([O:11][C:12](=O)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]([C:36](=[O:40])[N:37]([CH3:39])[CH3:38])[CH2:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)C.FC(F)(F)C(O)=O>O.C(OCC)(=O)C>[CH3:39][N:37]([CH3:38])[C:36](=[O:40])[CH:28]([C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][C:12](=[O:11])[NH:5][C:6]([NH2:8])=[O:7])=[CH:20][CH:19]=2)=[CH:23][CH:24]=1)[CH2:29][C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 1176UreaHCID 6422Trifluoroacetic acidHCID 2723922Sodium ethoxideHCID 59645434HCID 59645434, compound2×

Product 1

HCID 59645413HCID 59645413, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of sodium ethoxide (21% w/w, 8.10 mL, 21.8 mmol) and ethyl acetate (0.6 mL) was refluxed for 30 min. Urea (1.30 g, 21.8 mmol) was added and heated till it dissolved completely. 3-{4-[4-(1-Dimethylcarbamoyl-2-pyridin-3-ylethyl)-phenoxy]-phenyl}-propionic acid ethyl ester, 80 (1.74 g, 3.80 mmol) was added and heated for 5 min at 80° C. Reaction mixture was cooled to room temperature, neutralized by trifluoroacetic acid and water (50 mL) was added and extracted with ethyl acetate (3×50 mL). Organic layer was washed with water (2×20 mL) and brine (50 mL). The compound was purified by silica gel chromatography and product was eluted with chloroform-methanol (97:3). Yield: 0.30 g (16.7%).

Workup

  1. temperaturewas refluxed for 30 min
  2. temperatureheated till it
  3. dissolutiondissolved completely
  4. customReaction mixture
  5. temperaturewas cooled to room temperature
  6. additionwas added
  7. extractionextracted with ethyl acetate (3×50 mL)
  8. washOrganic layer was washed with water (2×20 mL) and brine (50 mL)
  9. customThe compound was purified by silica gel chromatography and product
  10. washwas eluted with chloroform-methanol (97:3)

Sources & evidence

ORD record
ord-9ad93ec1215241719818e9e861406a5c
Source dataset
uspto-grants-2008_01
Patent number
US07323496B2

Reaction notes

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