4-Chlorobenzylamine → HCID 15923149, compound

HRID 1861806Notes

Reaction equation

HRID 1861806 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.O.OC1C2N=NNC=2C=CC=1.[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.CCCCCC.C(OCC)(=O)C>CN(C=O)C.C(OCC)(=O)C>[Cl:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[N:7][CH:6]=3)[N:1]=2)=[O:13])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 660364-ChlorobenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 21226206Ethyl acetate hexaneHCID 178526939HCID 178526939, compound

Product 1

HCID 15923149HCID 15923149, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhydrous DMF (6.3 mL) at room temperature was added sequentially-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 4-chlorobenzyl amine (53.5 μL, 0.431 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarboiimide hydrochloride (61.8 mg, 0.316 mmol). The resulting mixture was allowed to stir at room temperature overnight and it was found to be clear. The solvent was removed under vacuum and the resulting residue was re-dissolved in CH2Cl2 (50 mL). The organic layer was washed with aqueous NaHCO3, dried over anhydrous Na2SO4, and concentrated to give the crude mixture. Flash column chromatography of the crude (50% hexane/ethyl acetate to 100% ethyl acetate) afforded the desired product as a white solid (80.3 mg, 94%): m.p. 110-111 ° C.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe resulting residue was re-dissolved in CH2Cl2 (50 mL)
  3. washThe organic layer was washed with aqueous NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the crude mixture

Sources & evidence

ORD record
ord-151a0745cc4d4b6ca4002c7f513451a2
Source dataset
uspto-grants-2003_03
Patent number
US06534520B2

Reaction notes

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