3-Oxabicyclo(3.1.0)hexane-2,4-dione → HCID 67128744, compound

HRID 449910Notes

Reaction equation

HRID 449910 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:18])[C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])[CH:5]=[CH:4][N:3]=1.[CH:19]12[CH2:24][CH:23]1[C:22](=[O:25])[O:21][C:20]2=O>O1CCOCC1>[Cl:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:17])[C:10]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:1]2[C:20](=[O:21])[CH:19]3[CH:23]([CH2:24]3)[C:22]2=[O:25])[CH:7]=1)=[O:18]

Participants

4

Reactant 2

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dioneHCID 59618313N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide

Product 1

HCID 67128744HCID 67128744, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(2-aminopyridin-4-yl)-2,6-dichlorobenzamide (1.41 g, 5 mmol) and 3-oxabicyclo[3.1.0]hexane-2,4-dione (2.24 g, 20 mmol) in 1,4-dioxane (25 mL) was heated at 90° C. for 4 hours. The reaction was cooled to room temperature and the precipitated white solid was collected by filtration to give 2,6-dichloro-N-(2-(−2,4-dioxo-3-azabicyclo[3.1.0]hexan-3-yl)pyridin-4-yl)benzamide (1.28 g, yield: 68%). 1H NMR (400 MHz, DMSO-d6) δ 11.42 (s, 1H), 8.47 (d, J=5.6 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.67-7.59 (m, 3H), 7.55 (dd, J=9.2, 6.8 Hz, 1H), 2.74 (dd, J=8.0, 3.6 Hz, 2H), 1.69 (ddt, J=20.6, 8.1, 4.2 Hz, 2H). LCMS (ESI) m/z: 376.0 [M+H+].

Workup

  1. filtrationthe precipitated white solid was collected by filtration

Sources & evidence

ORD record
ord-2c9c0b0594e84265a0c1affc7bbae709
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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