Benzylamine → HCID 485000, compound

HRID 1383400Notes

Reaction equation

HRID 1383400 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.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.CN(C)CCCN=C=NCC>C1COCC1.CCOC(C)=O.CN(C=O)C>[CH2:25]([NH:32][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])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 485000HCID 485000, compoundYield 128.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), 1-hydroxybenzo-triazole hydrate (42.7 mg, 0.316 mmol), benzylamine (45 mg, 0.42 mmol) in anhydrous THF (5 ml) at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60.6 mg, 0.316 mmol). The resulting mixture was allowed to stir at RT. After 20 min, DMF (2ml) was added to the reaction mixture and the 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 (100 ml). The organic layer was washed with aqueous NaHCO3, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (97 mg, 99%): m.p. 113-115° C.

Workup

  1. stirringto stir at room temperature overnight
  2. customThe solvent was removed under vacuum
  3. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  4. washThe organic layer was washed with aqueous NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customto give the crude mixture

Sources & evidence

ORD record
ord-2517e5e1bb1a4fc98356522b456f4e1b
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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