Hydrochloric Acid → HCID 71812093, compound

HRID 1752037Notes

Reaction equation

HRID 1752037 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:16][C:17]([C:19]2[CH:20]=[C:21]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[F:33])[CH:22]=[CH:23]C=2O)=[O:18])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Cl>O1CCCC1.N1C=CC=CC=1>[F:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[C:21]1[CH:22]=[CH:23][C:5]2[O:4][C:2](=[O:3])[N:16]([C:10]3[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=3)[C:17](=[O:18])[C:19]=2[CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 71812073HCID 71812073, compound

Product 1

HCID 71812093HCID 71812093, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

A solution of methyl chloroformate (1.2 mL, 12 mmol) was added drop wised to a stirred solution of compound 11 (1.54 g, 4 mmol) in dry anhydrous tetrahydrofuran/pyridine (30 mL) at 0° C. The mixture was refluxed for 3 h. After 10 h stirring at room temperature, the pH value of the mixture was adjusted to pH=6 by 5% HCl(aq). The mixture was cooled to obtain crystalline compound on an ice bath for 2-3 h. After cooling, precipitated crystals were filtered off and washed with diluted HCl and water. The crude product was purified by crystallization from hot ethanol to afford compound 23.

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. temperatureThe mixture was cooled
  3. customto obtain crystalline compound on an ice bath for 2-3 h
  4. temperatureAfter cooling
  5. customprecipitated crystals
  6. filtrationwere filtered off
  7. washwashed with diluted HCl and water
  8. customThe crude product was purified by crystallization from hot ethanol

Sources & evidence

ORD record
ord-ed6ad35054784bf78aa0f7ab5968f7c5
Source dataset
uspto-grants-2015_10
Patent number
US09162993B2

Reaction notes

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