Triethylamine → N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-propionamide

HRID 131351Notes

Reaction equation

HRID 131351 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3]1=[O:14].C(N(CC)CC)C.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>CN(C=O)C>[O:9]=[C:8]1[NH:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[NH:4][C:3](=[O:14])[CH:2]1[NH:1][C:22](=[O:25])[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58860686N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazapin-3-yl)-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3-amino-1H-1,5-benzodiazepine-2,4-(3H, 5H)-dione (5.7 g, 30.0 mmol) and triethyl amine(3.33 g, 33.0 mmol) in 120 mL DMF and add propionyl chloride dropwise at RT. After stirrng overnight, remove DMF under reduced pressure, suspend the residue in a mixed solvent (CHCl3/i-PrOH=3/1, 400 mL). Collect an off-white solid via suction filtration to give the title compound. Wash the filtrate with NaHCO3 (sat.2×100 mL) and dry with Na2SO4. Concentrate the organic solvent down to a residue, treat with ether, collect the solid: mass spectrum (APCI) (m/e): 248.1 (M+1). 1H NMR (400 MHz, DMSO-d6): δ 10.70 (s, 2H), 8.19 (d, 1H, J=7.2 Hz), 7.23-7.15 (m, 4H), 4.73 (d, 1H, J=8.0 Hz), 2.27 (q, 2H, J=8.0 Hz), 0.94 (t, 3H, J=8.0 Hz).

Workup

  1. customremove DMF under reduced pressure
  2. customCollect an off-white solid
  3. filtrationvia suction filtration

Sources & evidence

ORD record
ord-353b4765a5444c77995bf135e0d5ddd1
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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