HCID 86718494, compound → HCID 57263819, compound

HRID 1485398Notes

Reaction equation

HRID 1485398 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:9](=[O:15])[CH2:10][C:11](OC)=[O:12]>CCO>[CH2:16]([N:8]1[C:9](=[O:15])[CH2:10][C:11](=[O:12])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 86718494HCID 86718494, compound

Product 1

HCID 57263819HCID 57263819, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

methyl 3-((2-aminophenyl)(benzyl)amino)-3-oxopropanoate (200 mg, 0.67 mmol) was dissolved in 10 mL of EtOH and cooled to 0° C., and Na metal (25 mg, 1.07 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated and the residue was purified by prep-TLC to give 1-benzyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione (160 mg, 89%). 1H NMR (300 MHz, DMSO): δ 2.89 (d, J=9.9 Hz, 1H), 3.03 (d, J=10.2 Hz, 1H), 3.46 (q, J=21 Hz, 2H), 6.68 (t, J=8.1 Hz, 1H), 6.84-6.91 (m, 2H), 7.08-7.28 (m, 6H).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-fbc1b18bc07343cda3a5d1def1247ef1
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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