Triethylamine → Pentanoic acid (2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-amide

HRID 131353Notes

Reaction equation

HRID 131353 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:8][CH:9]1[C:15](=[O:16])[NH:14][C:13]2[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=2[NH:11][C:10]1=[O:21].C(N(CC)CC)C>CN(C)C=O>[O:21]=[C:10]1[NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[NH:14][C:15](=[O:16])[CH:9]1[NH:8][C:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 219558063-amino-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Product 1

HCID 58860632Pentanoic acid (2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add valeryl chloride (3.92 mL, 33.0 mmol) dropwise to a solution of 3-amino-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (5.74 g, 30.0 mmol) and triethylamine (4.60 mL, 33.0 mmol) in anhydrous dimethylformamide (123 mL) and stir. After 6 hours, concentrate under reduced pressure to a residue and reconstitute the residue in a solution of isopropanol: chloroform (1:3, 500 mL). Stir overnight to give a solid and isolate the solid by suction filtration, washing the solid with dichloromethane. Vacuum dry the solid at ambient temperature 2 hours to afford the title compound. Wash the filtrate with a saturated aqueous solution of sodium bicarbonate (2×200 mL), and filter the extraction mixture to remove salt formed in the wash. Separate the organic phase and wash it with saturated aqueous sodium chloride (150 mL). Back extract the bicarbonate aqueous phase with dichloromethane. Combine all organics, and dry (sodium sulfate), filter, and concentrate under reduced pressure to a residue. Triturate the residue in diethyl ether, filter the resulting solid, and wash it with diethyl ether; repeat 2×. Dry the solid at ambient temperature under vacuum to give the title compound: mass spectrum (APCI, m/e): 276 (M+1); NMR (1H, 300 MHz, DMSO-d): δ 10.68 (s, 2H), 8.23 (d, 1H, J=7.5 Hz), 7.20 (m, 4H), 4.71 (d, 1H, J=7.5 Hz), 2.25 (t, 2H, J=7.5 Hz), 1.43 (m, 2H), 1.25 (m, 2H), 0.83 (t, 3H, J=7.5 Hz).

Workup

  1. concentrationconcentrate under reduced pressure to a residue
  2. stirringStir overnight
  3. customto give a solid
  4. customisolate the solid
  5. filtrationby suction filtration
  6. washwashing the solid with dichloromethane
  7. customVacuum dry the solid at ambient temperature 2 hours

Sources & evidence

ORD record
ord-ef4c8653b55f4af88d6aecdf33e9d812
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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