4-amino-3-methylbenzamide → HCID 67176382, compound

HRID 2362240Notes

Reaction equation

O=[C:2]([CH2:10][CH2:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])=[CH:15][CH:14]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[CH:29][C:28]=1[CH3:36]>CCO.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Zn+2]>[C:31]([C:30]1[CH:34]=[CH:35][C:27]([N:26]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:2]2[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:28]([CH3:36])[CH:29]=1)(=[O:32])[NH2:33]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of ethyl 4,7-dioxo-7-(4-(2-oxooxazolidin-3-yl)phenyl)heptanoate (158 mg, 0.43 mmol) and 4-amino-3-methylbenzamide (130 mg, 0.68 mmol) in EtOH (1 mL) was added Zn(OTf)2 (313 mg, 0.86 mmol.). The mixture was heated to 120° C. under microwave for 2 h. After evaporation under reduced pressure, the crude product was purified by silica gel column chromatography (DCM:MeOH=20:1) to afford the titled compound as a yellow solid (77 mg, yield 39%).

Workup

customAfter evaporation under reduced pressure
customthe crude product was purified by silica gel column chromatography (DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-dbd7264925d74d2ab16a95cc94c23900
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691816B2

Reaction notes

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