Hydrochloric Acid → HCID 86632300, compound

HRID 2387228Notes

Reaction equation

HRID 2387228 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8](C#N)[C:9]2[CH:10]=[CH:11][C:12]([F:17])=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:4]([CH3:20])[C:3]=1[CH3:21].Cl.O>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([F:17])=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:4]([CH3:20])[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86646539HCID 86646539, compound

Product 1

HCID 86632300HCID 86632300, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Intermediate B1 was suspended in a mixture of acetic acid, conc. aq. HCl and water (1:1:2, 0.07M). The suspension was stirred and heated at reflux for 75 min. The reaction mixture was cooled to RT and the solvents were removed under reduced pressure. To the residue was added saturated aq. NaHCO3 and the mixture was extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated to dryness. The residue was purified by column chromatography on silica gel, eluting with PE-EtOAc (10-80% EtOAc) to afford the title compound as a yellow solid. MS (ES) C14H11ClFN3 required: 275, found: 276 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureat reflux for 75 min
  3. customthe solvents were removed under reduced pressure
  4. additionTo the residue was added saturated aq. NaHCO3
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with PE-EtOAc (10-80% EtOAc)

Sources & evidence

ORD record
ord-584c71b0bd52427386d29ea7aa7a3bb4
Source dataset
uspto-grants-2012_09
Patent number
US08268827B2

Reaction notes

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