tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate → 2-Oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile

HRID 885070Notes

Reaction equation

HRID 885070 reaction equation
[C:1]([C:3]1[C:4](=[O:26])[N:5]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:6]2[CH2:7][CH2:8][N:9](C(OC(C)(C)C)=O)[CH2:10][C:11]=2[CH:12]=1)#[N:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:26]=[C:4]1[C:3]([C:1]#[N:2])=[CH:12][C:11]2[CH2:10][NH:9][CH2:8][CH2:7][C:6]=2[N:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 58026066tert-butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 580260402-Oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-cyano-2-oxo-1-phenyl-1,2,7,8-tetrahydro-1,6-naphthyridine-6(5H)-carboxylate (150 mg, 0.427 mmol) was dissolved in CH2Cl2 (3 mL) and TFA (0.3 mL). The mixture was stirred at room temperature overnight. All solvents were removed under vacuum to give crude 2-oxo-1-phenyl-1,2,5,6,7,8-hexahydro-1,6-naphthyridine-3-carbonitrile. LCMS: m/z 252.15 (M+H)+, 0.78 min (method 7).

Workup

  1. customAll solvents were removed under vacuum

Sources & evidence

ORD record
ord-52b13d8314a34521880b9aadc57af4e6
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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