Benzoyl chloride → N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-(2-pyridin-3-ylethyl)benzamide hydrochloride

HRID 68964Notes

Reaction equation

HRID 68964 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:12]1[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[C:16](=[O:22])[N:15]([CH3:23])[C:14]2[CH:24]=[C:25]([CH2:28][NH:29][CH2:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[CH:26]=[CH:27][C:13]1=2)[CH3:11].C(=O)([O-])O.[Na+].C(O)C.Cl>C(O)(C)C.C(N(CC)CC)C.C(#N)C>[ClH:9].[CH2:10]([N:12]1[C:18](=[O:19])[C:17]([CH3:21])([CH3:20])[C:16](=[O:22])[N:15]([CH3:23])[C:14]2[CH:24]=[C:25]([CH2:28][N:29]([CH2:30][CH2:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:26]=[CH:27][C:13]1=2)[CH3:11]

Participants

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 21887872Ethanol hydrochlorideHCID 669599071-Ethyl-3,3,5-trimethyl-7-[(2-pyridin-3-yl-ethylamino)methyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 66960481N-(1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-7-ylmethyl)-N-(2-pyridin-3-ylethyl)benzamide hydrochloride

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Benzoyl chloride (0.13 ml) was added to an acetonitrile solution (6 ml) of 1-ethyl-3,3,5-trimethyl-7-[(2-pyridin-3-ylethylamino)methyl]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.38 g) and triethylamine (0.17 ml) under ice cooling. The mixture was stirred at room temperature overnight. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction by ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=91:9). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride ethanol solution (0.87 ml) was added to an isopropyl alcohol solution (10 ml) of the residue, and the liquid was condensed under reduced pressure. The residue was recrystallized from the ethanol-ether mixture to give the title compound (0.26 g) as a pale brown white powder.

Workup

  1. extractionfollowed by extraction by ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate, and condensed under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=91:9)
  4. customcondensed under reduced pressure
  5. customcondensed under reduced pressure
  6. customThe residue was recrystallized from the ethanol-ether mixture

Sources & evidence

ORD record
ord-664ff712efed47f8bd7643fd191979f4
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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