Cyclohexene → HCID 178432325, compound

HRID 220989Notes

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:45]=[CH:44][C:27]([CH2:28][NH:29][C:30]([CH:32]4[CH2:37][CH2:36][N:35]([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:34][CH2:33]4)=[O:31])=[C:26]([CH3:46])[CH:25]=3)=[O:23])[CH2:13][CH2:12][C:11]=2[N:10]=[C:9]1[CH3:47])C1C=CC=CC=1.C1CCCCC=1>C(O)C.[Pd]>[CH3:46][C:26]1[CH:25]=[C:24]([C:22]([N:14]2[CH2:13][CH2:12][C:11]3[N:10]=[C:9]([CH3:47])[NH:8][C:17]=3[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]2=3)=[O:23])[CH:45]=[CH:44][C:27]=1[CH2:28][NH:29][C:30]([CH:32]1[CH2:33][CH2:34][N:35]([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:36][CH2:37]1)=[O:31]

Participants

Conditions

Temperature: 60 °C

Procedure

1-(3,3-Dimethyl-butyl)-piperidine-4-carboxylic acid 4-(1-benzyl-2-methyl-4,5-dihydro-1H-1,3,6-triaza-benzo[e]azulene-6-carbonyl)-2-methyl-benzylamide from Example E121 (110 mg, 0.17 mmol) was dissolved in absolute ethanol (5 ml) and placed under an inert atmosphere. 10% Palladium on carbon (110 mg) and cyclo-hexene (0.176 ml, 1.7 mmol) were added and the mixture was heated at 60° C. for 3 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 powder identified as the title compound (45 mg, 48%).

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 powder

Sources & evidence

ORD record: ord-2b64f4a38b524710b79486f5cc104758
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202858B2

Reaction notes

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