Triethylamine → 6-Oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carbonitrile

HRID 656923Notes

Reaction equation

HRID 656923 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]([NH2:14])=O)=[CH:5][C:4]=2[N:3]1[CH2:15][CH:16]=[CH2:17].C(N(CC)CC)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]([C:12]#[N:14])=[CH:5][C:4]=2[N:3]1[CH2:15][CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 67749Trifluoromethanesulfonic anhydride2×HCID 516892Sodium BicarbonateHCID 688195936-Oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxamide

Product 1

HCID 688183616-Oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carbonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-oxo-5-(2-propen-1-yl)-5,6-dihydro-1,5-naphthyridine-3-carboxamide (0.69 g, 3 mmol) in DCM (30 ml) at 0° C. was added triethylamine (1.0 ml, 7.2 mmol) and trifluoromethanesulfonic anhydride (0.605 ml, 3.6 mmol) and the reaction was allowed warm to rt and stirred for 1 h at rt. Another four sequential treatments of triethylamine (1.0 ml, 7.2 mmol) and trifluoromethanesulfonic anhydride (0.605 ml, 3.6 mmol) over the next 6 h were necessary to drive the reaction almost to completion. The reaction mixture was treated with sat. aq NaHCO3 and the aqueous extracted twice more with DCM. The combined organic phases were then dried, evaporated and the residue was subjected to column chromatography on silica gel using a EtOAc:hexane gradient to provide the desired compound (0.570 g, 90%).

Workup

  1. customover the next 6 h
  2. customthe reaction almost to completion
  3. extractionthe aqueous extracted twice more with DCM
  4. customThe combined organic phases were then dried
  5. customevaporated

Sources & evidence

ORD record
ord-62a683d80efd41f098ad3f096eb1bad5
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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