Hydrochloric Acid → HCID 71812092, compound

HRID 1752038Notes

Reaction equation

HRID 1752038 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[C:14]1[CH:19]=[CH:18]C(O)=[C:16]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)=[O:22])[CH:15]=1.Cl>O1CCCC1.N1C=CC=CC=1>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][C:5]2[O:4][C:2](=[O:3])[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=3)[C:21](=[O:22])[C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 71812074HCID 71812074, compound

Product 1

HCID 71812092HCID 71812092, compoundYield 12%

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 12 (1.42 g, 4 mmol) in dry anhydrous tetrahydrofuran/pyridine (30 mL) at 0□. 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 24.

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-f634f04e490d44fd945ce287def9523b
Source dataset
uspto-grants-2015_10
Patent number
US09162993B2

Reaction notes

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