Benzoyl chloride → N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-benzamide

HRID 1066781Notes

Reaction equation

HRID 1066781 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1.C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[CH3:12][N:8]1[CH2:7][CH2:6][C:5]2[N:4]=[CH:3][C:2]([NH:1][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:11][C:10]=2[CH2:9]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

Product 1

HCID 21196427N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-benzamideYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine (314 mg, 1.9 mmol) was dissolved in dichloromethane (10 ml) and treated sequentially with triethylamine (214 mg; 2.1 mmol) and benzoyl chloride (297 mg; 2.1 mmol). The mixture was stirred at ambient temperature until tlc showed no starting material remaining. The reaction mixture was washed with saturated aqueous sodium hydrogen carbonate, water, saturated brine, dried (anhydrous magnesium sulphate) and evaporated to dryness under reduced pressure. Chromatography through silica gel, eluting with methanol in dichloromethane (0 to 50% methanol gradient), gave the title compound as an off-white foam (269 mg; 52%)

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate, water, saturated brine
  2. dry with materialdried (anhydrous magnesium sulphate)
  3. customevaporated to dryness under reduced pressure
  4. washChromatography through silica gel, eluting with methanol in dichloromethane (0 to 50% methanol gradient)

Sources & evidence

ORD record
ord-9a6127d327384485b112e23105a049cd
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

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