HCID 117667637, compound → HCID 117667561, compound

HRID 712598Notes

Reaction equation

HRID 712598 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]=[C:22]([C:24](=[O:26])[CH3:25])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:16]1[C:17]2[NH:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=[C:14]([C:18]2[CH:23]=[C:22]([C:24](=[O:26])[CH3:25])[CH:21]=[N:20][CH:19]=2)[CH:15]=1

Participants

4

Reactant 1

HCID 117667637HCID 117667637, compound

Product 1

HCID 117667561HCID 117667561, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

6-(5-Acetyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (500 mg, 1.4 mmol) is dissolved in 20 mL of 20% TFA in DCM. The mixture is stirred at room temperature for 16 hrs. Then the solvent and the extra reagent are removed and the residue is purified by reversed phase chromatography to give 135 mg of 1-[5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-ethanone

Workup

  1. customThen the solvent and the extra reagent are removed
  2. customthe residue is purified by reversed phase chromatography

Sources & evidence

ORD record
ord-44cc6042d1a242d586204fb235238e94
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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