Cyclohexene → HCID 178432324, compound

HRID 220991Notes

Reaction equation

C([N:8]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]([C:22]([C:24]3[CH:36]=[CH:35][C:27]([CH2:28][NH:29][C:30]([CH:32]4[CH2:34][CH2:33]4)=[O:31])=[C:26]([CH3:37])[CH:25]=3)=[O:23])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:38])C1C=CC=CC=1.C1C=C2C(N/N=C3/C4C=CC(S([O-])(=O)=O)=CC=4C=C(S([O-])(=O)=O)C/3=O)=CC=C(S([O-])(=O)=O)C2=CC=1.[Na+].[Na+].[Na+].N1CCCC(=O)C2C=CC=CC1=2.C1CCCCC=1>C(O)C.[Pd]>[CH3:37][C:26]1[CH:25]=[C:24]([C:22]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:38])[NH:8][C:17]=3[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=3)=[O:23])[CH:36]=[CH:35][C:27]=1[CH2:28][NH:29][C:30]([CH:32]1[CH2:33][CH2:34]1)=[O:31]

Participants

Conditions

Temperature: 60 °C

Procedure

Cyclopropanecarboxylic acid 4-(1-benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulene-6-carbonyl)-2-methyl-benzylamide from Example E123.1 (155 mg, 0.31 mmol) was dissolved in absolute ethanol (10 ml) and placed under an inert atmosphere. 10% Palladium on car-bon (155 mg) and cyclohexene (0.311 ml, 3.1 mmol) were added and the mixture was heated at 60° C. for 18 h. The catalyst was filtered off through Celite® filter agent and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane) to give a white solid identified as the title compound (67 mg, 53%).

Workup

filtrationThe catalyst was filtered off through Celite®
filtrationfilter agent
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified by preparative HPLC (eluant; 0.5% 35% ammonia:9.5% methanol:90% dichloromethane)
customto give a white solid

Sources & evidence

ORD record: ord-83e7110de6ec492681a1c858c0ede47f
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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