Acetic Acid → HCID 11645253, compound

HRID 736451Notes

Reaction equation

HRID 736451 reaction equation
[CH3:1][C:2]([OH:4])=O.[CH:5](=[C:12]1/[CH2:13][O:14][C:15]2[C:20]([C:21]/1=O)=[CH:19][C:18]([F:23])=[CH:17][CH:16]=2)/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[NH2:25][NH2:26]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[C:2]([N:25]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]2[CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([F:23])=[CH:19][C:20]=3[C:21]2=[N:26]1)(=[O:4])[CH3:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 57849017(3E)-6-Fluoro-2,3-dihydro-3-(phenylmethylene)-4H-1-benzopyran-4-one

Product 1

HCID 11645253HCID 11645253, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
175 °C

Procedure

A 5 mL microwave tube was charged with 4 mL AcOH, 1-1 (0.50 g, 2 mmol), and hydrazine monohydrate (0.2 mL, 3.93 mmol). The tube was sealed and heated in a Personal Chemistry microwave apparatus for 15 min at 175° C. LC/MS analysis indicated two new products with the same molecular weight. The reaction was diluted with EtOAc and neutralized with 200 mL saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. The remaining oil was absorbed onto silica gel and the diastereomers were separated on an Isco automated system affixed with a Biotage Flash 25(M) cartridge eluting at 20 mL/min with 15% EtOAc in hexane over 1 h. The diastereomer with the higher inhibitory activity (the cis) eluted second.

Workup

  1. customThe tube was sealed
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe remaining oil was absorbed onto silica gel
  6. customthe diastereomers were separated on an Isco automated system
  7. washeluting at 20 mL/min with 15% EtOAc in hexane over 1 h
  8. washThe diastereomer with the higher inhibitory activity (the cis) eluted second

Sources & evidence

ORD record
ord-8f055ccaacb5488482c81e4dd3b73d5c
Source dataset
uspto-grants-2009_09
Patent number
US07595337B2

Reaction notes

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