Benzylamine → HCID 483318, compound

HRID 1586501Notes

Reaction equation

HRID 1586501 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CN=CC=2)C=C[C:22]=1C(O)=O.O.ON1C2C=CC=CC=2N=N1.C(N)C1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>CCOC(C)=O.CN(C=O)C.C1COCC1>[CH3:22][C:7]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:1][NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)=[O:10]

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 485000HCID 485000, compoundHCID 7359081,6-Naphthyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 483318HCID 483318, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

compound #2 N-benzyl-2-[1,6]naphthyridinecarboxamide 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 anhy. 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 (2 ml) 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 aq. NaHCO3, 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 (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 aq. NaHCO3
  5. customdried over anhy
  6. concentrationMgSO4, and concentrated
  7. customto give the crude mixture

Sources & evidence

ORD record
ord-b09471aa1709414eae920d72608a4f3f
Source dataset
uspto-grants-1999_08
Patent number
US05945431

Reaction notes

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