Boron trifluoride etherate → HCID 178513152, compound

HRID 2203329Notes

Reaction equation

HRID 2203329 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[F:19].[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.B(F)(F)F.CCOCC>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1/[C:9](=[N:25]\[NH:24][C:21](=[NH:22])[NH2:23])/[CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[F:19]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 58425693HCID 58425693, compoundHCID 178418668HCID 178418668, compound2×

Product 1

HCID 178513152HCID 178513152, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a screw cap pressure vessel was added the intermediate from Step A (800 mg, 2.20 mmol), aminoguanidine hydrochloride (280 mg, 2.53 mmol), methanol (20 mL) and boron trifluoride diethyl etherate (0.63 mL, 4.95 mmol). After stirring at 100° C. for 1 hour, boron trifluoride diethyl etherate (1 mL) and aminoguanidine hydrochloride (200 mg) were added and the reaction solution heated at 100° C. for 3 hours. The solution was concentrated and the residue partitioned between EtOAc and aqueous 1N NaOH. The organic phase was washed with aqueous 1N NaOH (2×), brine and dried over anhydrous sodium sulfate. The solution was then filtered and concentrated to give the indicated product. m/z=419 (M+H).

Workup

  1. customTo a screw cap pressure vessel
  2. temperaturethe reaction solution heated at 100° C. for 3 hours
  3. concentrationThe solution was concentrated
  4. customthe residue partitioned between EtOAc and aqueous 1N NaOH
  5. washThe organic phase was washed with aqueous 1N NaOH (2×), brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solution was then filtered
  8. concentrationconcentrated
  9. customto give the indicated product

Sources & evidence

ORD record
ord-e4bd3aff8f2b46969c8f834425cd613a
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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