Hydrochloric Acid → HCID 178517380, compound

HRID 1851149Notes

Reaction equation

HRID 1851149 reaction equation
S(O)(O)(=O)=O.[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH2:11].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21])=[CH:15][CH:14]=1.N12CCCN=C1CCCCC2.Cl>CN(C=O)C.O>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[C:25]([OH:26])=[N:11][C:7]3[N:6]([CH:10]=[CH:9][N:8]=3)[C:20]=2[OH:21])=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 2782660Diethyl 2-(4-fluorophenyl)malonate

Product 1

HCID 178517380HCID 178517380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

7.2 g (39.3 mmol) 1H-Imidazol-2-ylamine sulfate are dissolved in 45 mL DMF. 10 g (39.3 mmol) diethyl (4-fluorophenyl)malonate is added. After dropwise addition of 17.6 mL (118 mmol) 1,8-diazabicyclo[5.4.0]undec-7-ene the reaction mixture is stirred at 100° C. over night. The DMF has been removed and the darkbrown oily residue treated with 150 mL water (complete dissolution). 2M HCl (60 mL) is added at room temperature until a pH of 1. After stirring for 1 h at ice bath cooling the formed crystals are collected by filtration to yield the product (5.78 g=53.9%), which is used without further purification. Another crop of 0.48 g (4.5%) is obtained by treating the solid residue in the flask with water and 2M HCl. After stirring for one hour the crystals are collected.

Workup

  1. customThe DMF has been removed
  2. additionthe darkbrown oily residue treated with 150 mL water (complete dissolution)
  3. addition2M HCl (60 mL) is added at room temperature until a pH of 1
  4. stirringAfter stirring for 1 h at ice bath
  5. temperaturecooling the formed crystals
  6. filtrationare collected by filtration
  7. customto yield the product (5.78 g=53.9%), which
  8. customis used without further purification
  9. customAnother crop of 0.48 g (4.5%) is obtained
  10. stirringAfter stirring for one hour the crystals
  11. customare collected

Sources & evidence

ORD record
ord-e8574d56889f49cfbed686ed7c5c9b92
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…