HCID 9839097, compound → HCID 54343162, compound

HRID 442694Notes

Reaction equation

HRID 442694 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11](=[O:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1.[O:23]([C:25]#[N:26])[Na]>C(O)(=O)C.CCOC(C)=O>[CH2:20]1[O:21][C:16]2=[CH:15][C:14]3[C:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:25]([NH2:26])=[O:23])=[CH:3][CH:4]=4)=[N:9][NH:10][C:11](=[O:22])[CH2:12][C:13]=3[CH:18]=[C:17]2[O:19]1

Participants

5

Reactant 2

HCID 9839097HCID 9839097, compoundHCID 178418852HCID 178418852, compound

Product 1

HCID 54343162HCID 54343162, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (119 mg, 0.403 mmol) in acetic acid (2 mL) was added NaOCN (38 mg, 0.58 mmol) at room temperature. The mixture was stirred at room temperature for 4 h, diluted with EtOAc (80 mL), washed with 2 N NaOH, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography to afford the title compound as a yellow solid (40 mg, 0.12 mmol, 30%), mp: 238°-241° C. 1H NMR (DMSO-d6) 10.79 (s, 1H), 8.77 (s, 1H), 7.47 (d, J=8.7, 2H), 7.40 (d, J=8.7, 2H), 7.07 (s, 1H), 6.61 (s, 1H), 6.10 (s, 2H), 5.95 (s, 2H), 3.33 (s, 2H).

Workup

  1. washwashed with 2 N NaOH, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-39275a37615d4c5f9ed18d8abf5bb6b8
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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