Methyl (+/-)-7-[[bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate → Methyl (+/-)-7-[[bis[2-(4-piperidinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate

HRID 613355Notes

Reaction equation

HRID 613355 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][N:9]([CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[NH:21][CH:20]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:19](=[O:27])[N:18]([CH3:28])[CH2:17][C:16]=3[CH:29]=2)=[O:11])=[CH:3][CH:2]=1>O=[Pt]=O.CO>[NH:35]1[CH2:36][CH2:37][CH:32]([CH2:31][CH2:30][N:9]([CH2:8][CH2:7][CH:4]2[CH2:3][CH2:2][NH:1][CH2:6][CH2:5]2)[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[NH:21][CH:20]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:19](=[O:27])[N:18]([CH3:28])[CH2:17][C:16]=3[CH:29]=2)=[O:11])[CH2:33][CH2:34]1

Participants

4

Reactant 1

HCID 53801004Methyl (+/-)-7-[[bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate

Product 1

HCID 54098965Methyl (+/-)-7-[[bis[2-(4-piperidinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetateYield 179.7%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl (±)-7-[[bis[2-(4-pyridinyl)ethyl]amino]carbonyl]-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (0.35 g, 0.65 mmole), PtO2 (0.11 g, 0.48 mmole), 1.0 N HCI (1.3 mL, 1.3 mmole), and MeOH (30 mL) was hydrogenated at 45 psi in a Parr apparatus. After 5 h, the reaction mixture was filtered through celite® and concentrated to give the crude title compound (0.6 g) which was used without further purification. MS(ES) m/e 514.4 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered through celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb7822146364833a57827bfede81407
Source dataset
uspto-grants-1999_12
Patent number
US06008214

Reaction notes

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