HCID 86754025, compound → HCID 18696524, compound

HRID 1420456Notes

Reaction equation

HRID 1420456 reaction equation
C(NC(=O)O)C1C=CC=CC=1.N[CH:13]1[C:19](=[O:20])[N:18]([CH2:21][C:22]([N:24]([CH:31]([CH3:33])[CH3:32])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]=2[C:15]([CH3:38])=[N:14]1>CO.[Pd]>[CH:31]([N:24]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:22](=[O:23])[CH2:21][N:18]1[C:17]2[CH:34]=[CH:35][CH:36]=[CH:37][C:16]=2[CH:15]([CH3:38])[NH:14][CH2:13][C:19]1=[O:20])([CH3:32])[CH3:33]

Participants

4

Reactant 1

HCID 86754025HCID 86754025, compound

Product 1

HCID 18696524HCID 18696524, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-(3-amino-5-methyl-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide benzyl carbamate (783 mg, 1.60 mmol) in methanol (16 mL) was added 10% palladium on carbon (320 mg). The resulting mixture was stirred under a hydrogen atmosphere for 15 h. The solids were removed by filtration through a pad of celite. The celite pad was washed with methanol and the filtrate concentrated in vacuo to give the titled compound (611 mg, 100%). Rf =0.04 (2/3 ethyl acetate/hexane); 1HNMR (300 MHz, CD3OD) d 1.06 (d, J=6.9 Hz, 3H), 1.08 (d, J=6.9 Hz, 3H), 1.47 (d, J=6.3 Hz, 3H), 3.18 (s, 2H), 4.07 (d, J=16.6 Hz, 1H), 4.20 (d, J=16.6 Hz, 1H), 4.43 (m, 1H), 7.21 (m, 1H), 7.34 (m, 6H), 7.51 (m, 3H).

Workup

  1. customThe solids were removed by filtration through a pad of celite
  2. washThe celite pad was washed with methanol
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f7be602c51ff40028bf69c161ec5b67c
Source dataset
uspto-grants-1999_03
Patent number
US05889182

Reaction notes

Loading…