Acetonitrile → HCID 59785897, compound

HRID 1673205Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:13][C:12](=[O:14])[C:11]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.[CH:26](=O)[CH:27](C)[CH3:28].N1CCC[CH2:32]1.C(#N)C>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[O:14][CH:17]([CH:27]([CH3:28])[CH3:26])[CH:16]([CH3:32])[C:15](=[O:18])[C:11]2=[CH:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-propionylpyridin-2(1H)-one (350 mg, 0.940 mmol), was added isobutyraldehyde (0.384. mL, 4.23 mmol), pyrrolidine (0.117 mL, 1.41 mmol) and acetonitrile (1.5 mL) The reaction was heated in a CEM Discover microwave system to 90° C. in a sealed microwave tube for 50 min. An additional charge of isobutyraldehyde (0.4 mL, 4.4 mmol) was added and the reaction was heated by microwave to 100° C. for 25 min and then 110° C. for 25 min. The reaction was diluted with EtOAc and washed with brine. The reaction was concentrated and the residue was purified by flash chromatography on silica gel gradient eluted with 0-60% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 426.1 (M+1), 428.1 (M+3); Rt=4.45 min.

Workup

additionwas added
temperaturethe reaction was heated by microwave to 100° C. for 25 min
washwashed with brine
concentrationThe reaction was concentrated
customthe residue was purified by flash chromatography on silica gel gradient
washeluted with 0-60% EtOAc in hexane

Sources & evidence

ORD record: ord-99f32d4aaedb471e8184da97619b0088
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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