Isopropyl iodide → HCID 53978012, compound

HRID 442679Notes

Reaction equation

HRID 442679 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.I[CH:24]([CH3:26])[CH3:25]>CN(C=O)C.CCOC(C)=O>[CH:24]([NH: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)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 6362Isopropyl iodideHCID 9839097HCID 9839097, compound

Product 1

HCID 53978012HCID 53978012, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-(4-aminophenyl)-7,8-methylenedioxy-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (110 mg, 0.373 mmol) in DMF (3 mL) was added 2-iodopropane (290 μL, 2.91 mmol). The mixture was stirred at 65° C. for two days, diluted with EtOAc (45 mL), washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography to afford the title compound as a tan solid (60 mg, 0.18 mmol, 48%), mp: 144°-146° C. 1H NMR (CDCl3) 8.20 (s, 1H), 7.41 (d, J=8.5, 2H), 6.81 (s, 1H), 6.74 (s, 1H), 6.56 (d, J=8.5, 2H), 6.02 (s, 2H), 3.80 (s, 1H), 3.69 (m, 1H), 3.42 (s, 2H), 1.24 (d, J=6.0, 6H).

Workup

  1. washwashed with 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-a956b3b8b16c4cfaa2b2181483597404
Source dataset
uspto-grants-1999_04
Patent number
US05891871

Reaction notes

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