HCID 117667606, compound → HCID 117667514, compound

HRID 712631Notes

Reaction equation

HRID 712631 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][C:23]=3[O:24][CH3:25])=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[CH3:25][O:24][C:23]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[C:14]1[CH:13]=[C:12]2[C:17](=[N:16][CH:15]=1)[NH:8][CH2:9][CH2:10][CH2:11]2

Participants

4

Reactant 1

HCID 117667606HCID 117667606, compound

Product 1

HCID 117667514HCID 117667514, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

6-(4-Methoxy-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (420 mg, 1.2 mmol) is dissolved in 20% trifluoroacetic acid in DCM (20 mL). The solution is stirred at room temperature for 16 hrs and then the solvent is removed. The residue is dissolved in DCM and saturated aqueous NaHCO3 solution is used to adjust the pH to 9˜10. The organic layer is separated, dried over Na2SO4, filtered and concentrated to give 290 mg of 6-(4-methoxy-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (290 mg crude) which is converted to 38 mg of the titled product according to the procedure of Urea Formation Method I.

Workup

  1. customthe solvent is removed
  2. dissolutionThe residue is dissolved in DCM
  3. customThe organic layer is separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3d48483fdec4ed981e393cb0d7ab834
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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