5-Propylcyclohexane-1,3-dione → HCID 67410243, compound

HRID 909392Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([S:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[C:9]=1[NH:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=O.[CH3:24]/[C:25](/[NH2:29])=[CH:26]\[C:27]#[N:28].[CH2:30]([CH:33]1[CH2:38][C:37](=O)[CH2:36][C:35](=[O:40])[CH2:34]1)[CH2:31][CH3:32]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:36]3[C:35](=[O:40])[CH2:34][CH:33]([CH2:30][CH2:31][CH3:32])[CH2:38][C:37]=3[NH:29][C:25]([CH3:24])=[C:26]2[C:27]#[N:28])[CH:7]=[C:8]([S:15]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)(=[O:17])=[O:16])[C:9]=1[NH:10][CH2:11][CH2:12][O:13][CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the product of step d (61 mg), 3-aminocrotonitrile (12.3 mg) and 5-propylcyclohexane-1,3-dione (23.1 mg) in ethanol (5 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC (Method B). Yield: 57 mg. MS-ESI: [M+H]+=607.3/609.3; HPLC: Rt=16.51 min. (diast. 1) Rt=16.83 min. (diast. 2) (method 1). Diast. ratio: 9:1

Workup

concentrationThe reaction mixture was concentrated in vacuo
customthe residue was purified by preparative HPLC (Method B)

Sources & evidence

ORD record: ord-b3007321c7f64c6fad9000e1d19d8875
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017782B2

Reaction notes

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