HCID 86685968, compound → HCID 178493743, compound

HRID 2277674Notes

Reaction equation

HRID 2277674 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9](=[O:13])[N:8]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=3)[CH2:7][CH2:6][C:5]=2[N:4]=1>Cl.O1CCOCC1>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9](=[O:13])[N:8]([C:14]3[CH:15]=[N:16][CH:17]=[C:18]([O:20][CH3:21])[CH:19]=3)[CH2:7][CH2:6][C:5]=2[N:4]=1

Participants

4

Reactant 1

HCID 86685968HCID 86685968, compound

Product 1

HCID 178493743HCID 178493743, compoundYield 1.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Methoxy-6-(5-methoxy-pyridin-3-yl)-7,8-dihydro-6H-[1,6]naphthyridin-5one (445 mg, 1.56 mmol) (example 97) was suspended in 2 mL of aq. conc. HCl in 1,4-dioxane (2:1) and heated at 80° C. for 3 hours before the solvent was removed in vacuo. After extraction between EtOAc and H2O, the organic layer was washed with aq. satd. NaHCO3 solution, brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by prep-HPLC to yield the title compound (4.9 mg) as a white solid. MS: 270.2 (M+H+).

Workup

  1. customwas removed in vacuo
  2. extractionAfter extraction between EtOAc and H2O
  3. washthe organic layer was washed with aq. satd
  4. dry with materialNaHCO3 solution, brine, dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo
  7. customto give a crude product which
  8. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-334c2a17a7bc4343989e2cf6ca149f16
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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