HCID 15937178, compound → HCID 54730528, compound

HRID 522374Notes

Reaction equation

HRID 522374 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:16])[CH2:10][C:11]([O:13]CC)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:16])[CH:10]=[C:11]2[OH:13]

Participants

3

Reactant 1

HCID 15937178HCID 15937178, compound

Product 1

HCID 54730528HCID 54730528, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of the product from step 1 (20.27 g) in DCM (100 ml) was added to polyphosphoric acid (43.7 ml). Dichloromethane was distilled from the reaction mixture by increasing the temperature slowly and then the brownish gummy solution was stirred at 120° C. for 3 hours and then left at room temperature for 16 hours. The reaction mixture was quenched by adding ice cooled water and the product was filtered. The filter cake was stirred with 500 mL of water and filtered to give the desired product (9.38 g) as a colorless solid. LRMS (ES+) m/z 180.1 (M+H)+.

Workup

  1. distillationDichloromethane was distilled from the reaction mixture
  2. temperatureby increasing the temperature slowly
  3. waitleft at room temperature for 16 hours
  4. customThe reaction mixture was quenched
  5. additionby adding ice
  6. temperaturecooled water
  7. filtrationthe product was filtered
  8. stirringThe filter cake was stirred with 500 mL of water
  9. filtrationfiltered

Sources & evidence

ORD record
ord-d832c0cb5b114035a8dc65383e5674d3
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

Loading…