6-(3,6-dihydro-2H-pyran-4-yl)-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine → 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-(tetrahydro-2H-pyran-4-yl)-1,8-naphthyridine

HRID 1778046Notes

Reaction equation

HRID 1778046 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][C:16]=2[CH:17]([O:20][CH3:21])[O:18][CH3:19])[NH:13][CH2:12][CH2:11][CH2:10]3)[CH2:3][CH2:2]1.[H][H]>C1COCC1.CO.[Pd]>[CH3:21][O:20][CH:17]([O:18][CH3:19])[C:16]1[N:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][NH:13]2)=[CH:8][C:7]=1[CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 1180369276-(3,6-dihydro-2H-pyran-4-yl)-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine2×HCID 178418361HCID 178418361, compound

Product 1

HCID 1180366867-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-(tetrahydro-2H-pyran-4-yl)-1,8-naphthyridine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10% Pd on carbon (0.34 g) in a solution of 6-(3,6-dihydro-2H-pyran-4-yl)-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 313, 0.94 g, 3.24 mmol) in THF (60 ml) and MeOH (20 ml) was stirred under an atmosphere of hydrogen at room temperature for 56 h, at which point 1 equivalent of hydrogen had been consumed. The reaction mixture was flushed with argon, filtered and evaporated to give the title compound as a beige solid. (UPLC-MS 3) tR 0.54 min; ESI-MS 293.3 [M+H]+.

Workup

  1. customhad been consumed
  2. customThe reaction mixture was flushed with argon
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2e58e43edd5f4a4887ea5d33bf30ecac
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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