Boron trifluoride etherate → HCID 12069536, compound

HRID 1355618Notes

Reaction equation

HRID 1355618 reaction equation
C(OC([NH:8][C:9]1[C:10]([NH:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:16]([NH:15][C:10]2[C:9]([NH2:8])=[CH:14][CH:13]=[CH:12][N:11]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12069535HCID 12069535, compound

Product 1

HCID 12069536HCID 12069536, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N3-(tert-butoxycarbonyl)-N2-(4-methoxy-benzoyl)-2,3-pyridinediamine (350 mg, 1.02 mmol) in acetic acid (2 mL) at 0° C. was treated with boron trifluoride etherate (0.50 mL, 4.1 mmol). After 2 h, the mixture was poured into aqueous sodium bicarbonate and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate and the combined extracts were dried (magnesium sulfate), filtered, and concentrated in vacuo. Purification of the residue by chromatography (silica gel, ethyl acetate/methylene chloride) yielded 122 mg (49%) of the title compound.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. dry with materialthe combined extracts were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by chromatography (silica gel, ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-a4945afdc474434faae91fda0332f79c
Source dataset
uspto-grants-2003_07
Patent number
US06586459B2

Reaction notes

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