Piperidine → [4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid tert-butyl ester

HRID 900139Notes

Reaction equation

[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:17](=[O:18])[CH2:16][C:15]2[N:11]([C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][N:14]=2)[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]1=2)([CH3:4])([CH3:3])[CH3:2].[NH:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([CH:39]=O)=[CH:31]1.N1CCCCC1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:17](=[O:18])[C:16](=[CH:39][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[NH:30][CH:31]=2)[C:15]2[N:11]([C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][N:14]=2)[C:10]2[CH:25]=[CH:26][CH:27]=[CH:28][C:9]1=2)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-acetic acid tert-butyl ester (Preparation 13(B)) (3.66 g, 9.37 mmol) in toluene (94 mL) was added 1H-indole-3-carbaldehyde (1.63 g, 11.2 mmol) and piperidine (2.78 mL, 28.1 mmol). The reaction was heated to 110° C. in a Soxhlet for 10 hours and was stirred at room temperature for 24 hours. The precipitate was filtered and was washed with toluene to provide 6.47 g of [4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-acetic acid tert-butyl ester. MS 518.5 (M+1).

Workup

filtrationThe precipitate was filtered
washwas washed with toluene

Sources & evidence

ORD record: ord-fc2d2b44d10b4de8ba7fde3658dc5c05
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07358242B2

Reaction notes

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