2-Chlorobenzylamine → N-(2-chlorobenzyl)-2-[1,6]naphthyridinecarboxamide

HRID 1586503Notes

Reaction equation

HRID 1586503 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.[Cl:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28][NH2:29].Cl.CN(C)CCCN=C=NCC>CCOC(C)=O.CN(C=O)C>[Cl: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 666482-ChlorobenzylamineHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 15923147N-(2-chlorobenzyl)-2-[1,6]naphthyridinecarboxamideYield 97.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol) in anhy. DMF (5 ml) at room temperature was sequentially added 1-hydroxybenzotriazole hydrate (42.7 mg, 0.316 mmol), 2-chlorobenzylamine (54.7 μl, 95%., 0.43 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (60.6 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 (100 ml). 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 (100 ml). The organic layer was washed with aq. Na(CO3, dried over anhy. 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 (83 mg, 97%): m.p. 120-121° C.

Workup

  1. customat room temperature
  2. customThe solvent was removed under vacuum
  3. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  4. stirringto stir at room temperature overnight
  5. customThe solvent was removed under vacuum
  6. dissolutionthe resulting residue was redissolved in CH2Cl2 (100 ml)
  7. washThe organic layer was washed with aq. Na(CO3
  8. customdried over anhy
  9. concentrationMgSO4, and concentrated
  10. customto give the crude mixture

Sources & evidence

ORD record
ord-530a9476aeb0413e9a0241810d2b2934
Source dataset
uspto-grants-1999_08
Patent number
US05945431

Reaction notes

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