Hydrochloric Acid → 2,6-difluoro-N-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide

HRID 1054909Notes

Reaction equation

HRID 1054909 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=[O:5].Cl>C(O)C.[Pd]>[F:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][NH:10][C:9]=2[N:8]=1)=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 900122172,6-difluoro-N-[1,8]naphthyridin-2-ylbenzamide

Product 1

HCID 900116482,6-difluoro-N-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2,6-Difluoro-N-[1,8]naphthyridin-2-ylbenzamide (35 mg, 0.12 mmol) and 10% Pd/C (15 mg) were suspended in ethanol (5 mL). Concentrated HCl (0.02 mL, 0.24 mmol) was then added and the reaction mixture was stirred under hydrogen (1 atmosphere) for three hours. Next, the reaction mixture was filtered through Celite and concentrated to give 2,6-difluoro-N-(5,6,7,8-tetrahydro[1,8]naphthyridin-2-yl)benzamide. Yield 33 mg (95%). LCMS (ESI): calc. C15H13F2N3O=289; obs. M+H=290.

Workup

  1. filtrationNext, the reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9f6f458cc5d7429b9ca504aaabd45ec0
Source dataset
uspto-grants-2016_07
Patent number
US09394315B2

Reaction notes

Loading…