Acetic Acid → N1-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-N2,N2-dimethylethane-1,2-diamine

HRID 1778003Notes

Reaction equation

HRID 1778003 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH:14]=O)=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1.[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22].CC(O)=O>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:16][CH3:17])[C:4]1[C:13]([CH2:14][NH:22][CH2:21][CH2:20][N:19]([CH3:23])[CH3:18])=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 1180364262-(Dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde2×

Product 1

HCID 118036618N1-((2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)methyl)-N2,N2-dimethylethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 1.5 g, 6.35 mmol) in DCM (40 ml) at room temperature was added 2-dimethylaminoethylamine (1.387 ml, 12.70 mmol) and AcOH (0.472 mL, 8.25 mmol), followed by Na(AcO)3BH (2.69 g, 12.70 mmol) and the reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was diluted with DCM, quenched with saturated aqueous NaHCO3 and stirred for 20 min. Phases were separated and the water phase was extracted with DCM. Organic phases were combined, dried using Na2SO4, filtered and concentrated. The crude product was purified via silica gel column chromatography eluting with a gradient of MeOH (0-15%) in DCM. Fractions containing the product were combined and concentrated to yield the title compound.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. stirringstirred for 20 min
  3. customPhases were separated
  4. extractionthe water phase was extracted with DCM
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified via silica gel column chromatography
  9. washeluting with a gradient of MeOH (0-15%) in DCM
  10. additionFractions containing the product
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a92443f03c864535a037e80cf9576f25
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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