4-{3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyloxymethyl}-piperidine-1-carboxylic Acid Benzyl Ester → 3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic Acid piperidin-4-ylmethyl Ester

HRID 220920Notes

Reaction equation

HRID 220920 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19](=[O:46])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]3[CH2:39][C:38]4[CH:37]=[N:36][N:35]([CH3:40])[C:34]=4[NH:33][C:32]4[CH:41]=[CH:42][CH:43]=[CH:44][C:31]3=4)=[O:29])=[CH:24][C:23]=2[CH3:45])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][C:19](=[O:46])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:30]3[CH2:39][C:38]4[CH:37]=[N:36][N:35]([CH3:40])[C:34]=4[NH:33][C:32]4[CH:41]=[CH:42][CH:43]=[CH:44][C:31]3=4)=[O:29])=[CH:24][C:23]=2[CH3:45])[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 1361284314-{3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyloxymethyl}-piperidine-1-carboxylic Acid Benzyl Ester

Product 1

HCID 1361284193-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic Acid piperidin-4-ylmethyl EsterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-{3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionyloxymethyl}-piperidine-1-carboxylic acid benzyl ester from Example E77.1 (44 mg, 0.07 mmol) was dissolved in methanol (5 ml) and hydrogenated over 10% Pd/C catalyst (5 mg) for 2 h. The mixture was filtered through Celite® filter agent and the filtrate concentrated in vacuo to give a white powder identified as the title compound (34 mg, 98%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a white powder

Sources & evidence

ORD record
ord-c7fcc22b7cc54c739542452fba22a5d2
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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