Boron trifluoride etherate → HCID 12069536, compound

HRID 428011Notes

Reaction equation

HRID 428011 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-methoxybenzoyl)-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-98bc2bb1092e457188b09009de673de6
Source dataset
uspto-grants-2001_11
Patent number
US06313151B1

Reaction notes

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