N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide → N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-propyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide

HRID 343198Notes

Reaction equation

HRID 343198 reaction equation
[CH:1]([N:4]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:5](=[O:36])[CH2:6][N:7]1[C:13](=[O:14])[C:12]([CH3:24])([CH2:15][CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:25])[N:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]2[CH:32]=[CH:33][CH:34]=[CH:35][C:8]1=2)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([N:4]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:5](=[O:36])[CH2:6][N:7]1[C:13](=[O:14])[C:12]([CH3:24])([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:25])[N:10]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:9]2[CH:32]=[CH:33][CH:34]=[CH:35][C:8]1=2)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67699497N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide

Product 1

HCID 67700209N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-propyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamideYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirring solution of 40 mg (71.7 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-5-phenyl-3-(3-phenyl-allyl)-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Example 11, in 3 mL absolute ethanol is added 10 mg of 10% palladium on carbon. The reaction vessel is placed on a Parr hydrogenation apparatus, evacuated, and then pressurized with H2 gas to 40 psi and shaken for 2 h at RT. The reaction mixture is filtered through Celite to remove the catalyst and the solvent removed in vacuo. Purification of the resulting material via reverse phase MPLC using a C-18 column and 70% acetonitrile/30% H2O with 0.1% TFA as eluent followed by lyophilization afforded 29 mg of the title compound as a white amorphous solid: 1H NMR (CDCl3, 300 MHz) δ7.49-6.96 (m, 19H), 6.72 (d, 1H, J=8.0), 5.09 (m, 1H), 4.38 (d, 1H, J=16.3), 3.92 (d, 1H, J=16.3), 2.28 (m, 2H), 1.67-1.50 (m, 6H), 1.34 (m, 1H), 1.12 (m, 6H); low resolution MS (FAB)m/e 560 (MH+), 425, 397, 223.

Workup

  1. customevacuated
  2. filtrationThe reaction mixture is filtered through Celite
  3. customto remove the catalyst
  4. customthe solvent removed in vacuo
  5. customPurification of the resulting material via reverse phase MPLC

Sources & evidence

ORD record
ord-8c188b648f8544de911b56e276320d89
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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