Hydrochloric Acid → HCID 71812075, compound

HRID 871825Notes

Reaction equation

HRID 871825 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:17]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])[CH:19]=[CH:20]C=2O)=[O:15])=[C:9]([F:31])[CH:8]=1.Cl>O1CCCC1.N1C=CC=CC=1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:14](=[O:15])[C:16]3[CH:17]=[C:18]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=4[F:30])[CH:19]=[CH:20][C:5]=3[O:4][C:2]2=[O:3])=[C:9]([F:31])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 86699694HCID 86699694, compound

Product 1

HCID 71812075HCID 71812075, compoundYield 11%

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 1 (1.5 g, 4 mmol) in dry anhydrous tetrahydrofuran/pyridine (30 mL) at 0° C. The mixture was refluxed for 2.5 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 13.

Workup

  1. temperatureThe mixture was refluxed for 2.5 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-e833225624dd436a9904ca472b487e5f
Source dataset
uspto-grants-2015_03
Patent number
US08975255B2

Reaction notes

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