N-Acetyl-4-piperidone → HCID 178473860, compound

HRID 536956Notes

Reaction equation

HRID 536956 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:18]2[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=2)[CH:3]=1.[C:26]([N:29]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31][CH2:30]1)(=[O:28])[CH3:27]>CO.C(Cl)Cl>[C:26]([N:29]1[CH2:34][CH2:33][C:32]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[NH:12][CH:13]=[C:14]([C:16]#[N:17])[N:15]=3)=[O:10])=[C:4]([C:18]3[CH2:23][CH2:22][C:21]([CH3:25])([CH3:24])[CH2:20][CH:19]=3)[CH:3]=2)([OH:35])[CH2:31][CH2:30]1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 122563N-Acetyl-4-piperidoneHCID 1784244434-Cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide

Product 1

HCID 178473860HCID 178473860, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 11 using 4-cyano-1H-imidazole-2-carboxylic acid [4-bromo-2-(4,4-dimethyl-cyclohex-1-enyl)-phenyl]-amide (as prepared in Example 1, step (g), 80.0 mg, 0.200 mmol) and 1-acetyl-piperidin-4-one (123 μL, 1.00 mmol). Silica gel chromatography (2-5% MeOH/DCM) afforded the title compound (59.1 mg, 64%) as a colorless oil. 1H-NMR (CD3OD; 400 MHz): δ 8.18 (d, 1H, J=8.6 Hz), 8.00 (s, 1H), 7.39 (dd, 1H, J=8.6, 2.3 Hz), 7.35 (d, 1H, J=2.3 Hz), 5.74 (m, 1H), 4.45 (m, 1H), 3.84 (m, 1H), 3.60 (m, 1H), 3.11 (m, 1H), 2.28-2.35 (m, 2H), 2.15 (s, 3H), 1.91-2.10 (m, 4H), 1.76 (m, 2H), 1.59 (t, 2H, J=6.3 Hz), 1.09 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C26H31N5O3, 462.2 (M+H). found 462.0.

Sources & evidence

ORD record
ord-49946154e24a448d8c0feaca1b06ff7e
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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