HCID 117667719, compound → HCID 117666971, compound

HRID 712632Notes

Reaction equation

HRID 712632 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[C:24]([O:26][CH3:27])=[O:25])=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>Cl.CO>[CH3:27][O:26][C:24](=[O:25])[C:23]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[C:14]1[CH:15]=[N:16][C:17]2[NH:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1

Participants

4

Reactant 1

HCID 117667719HCID 117667719, compound

Product 1

HCID 117666971HCID 117666971, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

6-(4-Methoxycarbonyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (400 mg, 1.1 mmol) is dissolved in 1.25 M HCl in MeOH (200 mL). The mixture is stirred at 30° C. for 16 hrs. The solvent is removed and the pH of the residue is adjusted to 9˜10 using saturated aqueous NaHCO3 solution. The mixture is then extracted with DCM and the organic layer is dried over Na2SO4, filtered and concentrated to give 214 mg of 3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-isonicotinic acid methyl ester which is used in the next step without further purification.

Workup

  1. customThe solvent is removed
  2. extractionThe mixture is then extracted with DCM
  3. dry with materialthe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-15aed783793340cf8c3ddb4b7516f25f
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…