4-Methoxybenzylamine → 2-(4-methoxybenzylamino)-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6-H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724926Notes

Reaction equation

HRID 724926 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:28])[C:7](=[O:27])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>>[CH3:29][O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:36][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH3:28])[C:7](=[O:27])[C:8]4[CH:18]=[C:17]([CH2:19][CH2:20][C:21]5[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=5)[CH:16]=[N:15][C:9]=4[N:10]([CH2:13][CH3:14])[C:11]=3[N:12]=2)=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 754524-MethoxybenzylamineHCID 4706665-Chloro-2-ethyl-9-methyl-13-[2-(pyridin-4-yl)ethyl]-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

Product 1

HCID 197111072-(4-methoxybenzylamino)-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6-H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 26%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.285 g, 0.7 mmol) and 4-methoxybenzylamine (0.23 mL, 1.8 mmol) in 4 mL of xylenes was heated at 150° C. in a sealed tube. After 24 hours, additional amine (0.23 mL, 1.8 mmol) was added and the reaction temperature was increased to 250° C. Heat was removed after 2d, and the reaction mixture was washed with saturated aqueous ammonium chloride to remove excess amine. The organic layer was dried (magnesium sulfate) and concentrated. Purification by flash chromatography (elution with methanol-dichloromethane) afforded the title compound (0.09 g, 26%).

Workup

  1. temperaturethe reaction temperature was increased to 250° C
  2. temperatureHeat
  3. customwas removed after 2d
  4. washthe reaction mixture was washed with saturated aqueous ammonium chloride
  5. customto remove excess amine
  6. dry with materialThe organic layer was dried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification
  9. washby flash chromatography (elution with methanol-dichloromethane)

Sources & evidence

ORD record
ord-41211b93722a4cc091d3e939ae59cce8
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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