HCID 59327640, compound → HCID 46214906, compound

HRID 1184036Notes

Reaction equation

HRID 1184036 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:28])([CH3:27])[C:9]([NH:11][NH:12][C:13]([C:15]2[C:16]([CH3:26])=[N:17][C:18]3[C:23]([C:24]=2[CH3:25])=[CH:22][CH:21]=[CH:20][CH:19]=3)=O)=[O:10])=[CH:4][CH:3]=1.COC(CC[N+](S(=O)(=O)N)(CC)CC)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]2[O:10][C:13]([C:15]3[C:16]([CH3:26])=[N:17][C:18]4[C:23]([C:24]=3[CH3:25])=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:12][N:11]=2)([CH3:27])[CH3:28])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 59327640HCID 59327640, compoundHCID 86641822HCID 86641822, compound

Product 1

HCID 46214906HCID 46214906, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-2,4-dimethylquinoline-3-carbohydrazide (592 mg, 1.5 mmol) in dry tetrahydrofuran (5 ml) was added Burgess's reagent (methoxycarbonyl-sulfamoyltriethylammonium inner salt; 714 mg, 3.0 mmol). The mixture was heated at 60° C. for 1 hour, diluted with ethyl acetate, and washed with water, saturated sodium bicarbonate, and then brine. The organic phase was separated, and the solvent removed under reduced pressure, to provide 2-(2-(4-chlorophenyl)propan-2-yl)-5-(2,4-dimethylquinolin-3-yl)-1,3,4-oxadiazole (205 mg, 36%) as a white powder. 1H NMR (CDCl3, 400 MHz) δ 8.03 (app t, 2H, J=8.2 Hz); 7.78 (app t, 1H, J=7.0 Hz); 7.58 (app t, 1H, J=7.0 Hz); 7.30 (app q, 4H); 2.56 (s, 3H); 2.51 (s, 3H); 1.90 (s, 6H). LCMS (CI) M+H 378.

Workup

  1. washwashed with water, saturated sodium bicarbonate
  2. customThe organic phase was separated
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-15f4a95a2f914254a3b9be967bd30742
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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