2-Fluorobenzylamine → HCID 15923148, compound

HRID 1586506Notes

Reaction equation

HRID 1586506 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.ON1C2C=CC=CC=2N=N1.[F:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][NH2:29].CCCCCC.C(OCC)(=O)C>CN(C=O)C.C(OCC)(=O)C>[F:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][NH:29][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1)=[O:13]

Participants

7

Reactant 4

HCID 666492-FluorobenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21226206Ethyl acetate hexane

Product 1

HCID 15923148HCID 15923148, compoundYield 98.1%

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 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 2-fluorobenzyl amine (51.0 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 redissolved in CH2Cl2 (50 mL). The organic layer was washed with aq. 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 (79.2 mg, 98%) m.p. 110-111° C.

Workup

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

Sources & evidence

ORD record
ord-c4a9497c0e85408ab710f0a40cc8dcc1
Source dataset
uspto-grants-1999_08
Patent number
US05945431

Reaction notes

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