(E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic Acid Tert-butyl Ester → 3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic Acid Tert-butyl Ester

HRID 220864Notes

Reaction equation

HRID 220864 reaction equation
[C:1]([O:5][C:6](=[O:33])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])=[CH:11][C:10]=1[CH3:32])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])=[CH:11][C:10]=1[CH3:32])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 136128393(E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic Acid Tert-butyl Ester

Product 1

HCID 1361283503-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-propionic Acid Tert-butyl EsterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-3-[2-Methyl-4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-phenyl]-acrylic acid tert-butyl ester from Example E45.2 (436 mg, 0.99 mmol) was dissolved in methanol (40 ml) and hydrogenated over 10% Pd/C catalyst (91 mg) for 5 h. The mixture was filtered through Celite® filter agent and the filtrate was concentrated in vacuo and azeotroped with dichloromethane to yield the title compound (426 mg, 96%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated in vacuo
  4. customazeotroped with dichloromethane

Sources & evidence

ORD record
ord-69d98a150bba4d06865d0400b05bb4b1
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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