Hydrochloric Acid → HCID 72192638, compound

HRID 1473828Notes

Reaction equation

HRID 1473828 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15](=[O:25])[C:16]1C=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1O.Cl>N1C=CC=CC=1>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[N:14]1[C:15](=[O:25])[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][C:5]=2[O:4][C:2]1=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 28393793HCID 28393793, compound

Product 1

HCID 72192638HCID 72192638, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl chloroformate (0.1 mL, 1.2 mmole) was added dropwise to a stirred solution of compound 4a (0.28 g, 1 mmole) in dry pyridine (8 mL) at 0° C. The mixture was refluxed for 2 hr. After 16 hr stirring at room temperature, the pH of the reaction mixture was adjusted to pH=6 from 1 M HCl(aq). The resulting white mixture was cooled to obtain solid compound. The product was filtered off and recrystallized from hot ethanol. The residue was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, then concentrated and recrystallized with hot methanol.

Workup

  1. temperatureThe mixture was refluxed for 2 hr
  2. temperatureThe resulting white mixture was cooled
  3. customto obtain solid compound
  4. filtrationThe product was filtered off
  5. customrecrystallized from hot ethanol
  6. extractionThe residue was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customrecrystallized with hot methanol

Sources & evidence

ORD record
ord-7a8e9002e7a5449fa2e066f58d6ea0cb
Source dataset
uspto-grants-2015_04
Patent number
US09018203B2

Reaction notes

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