Acetic Acid → HCID 86716490, compound

HRID 1747716Notes

Reaction equation

HRID 1747716 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]#[N:15])[N:6]=1.C[O-].[Na+].[Cl-].[NH4+:24].[C:25]([OH:28])(=[O:27])[CH3:26]>CO>[C:25]([OH:28])(=[O:27])[CH3:26].[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[N:9]2[N:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14](=[NH:24])[NH2:15])[N:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 70983445HCID 70983445, compound

Product 1

HCID 86716490HCID 86716490, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

584 mg (2.315 mmol) of the compound prepared in Example 6A were added to 125 mg (2.315 mmol) of sodium methoxide in methanol (10 ml), and the mixture was stirred at 20° C. for 16 hours. 148 mg (2.778 mmol) of ammonium chloride and acetic acid (0.517 ml) were then added, and the mixture was heated at reflux for 8 h. The mixture was then concentrated to dryness, the residue was taken up in water and ethyl acetate and 1 N aqueous sodium hydroxide solution was added. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, concentrated and then dried under high vacuum. This gave 543 mg of the target compound (71% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 8 h
  3. concentrationThe mixture was then concentrated to dryness
  4. additionethyl acetate and 1 N aqueous sodium hydroxide solution was added
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-daf04a1e4cc84db88e013120f4046eec
Source dataset
uspto-grants-2015_10
Patent number
US09150580B2

Reaction notes

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