N,N'-Dimethylethylenediamine → HCID 89814176, compound

HRID 525337Notes

Reaction equation

HRID 525337 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[NH:4][CH:3]1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.I[C:16]1[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=2[N:31]=[CH:30][CH:29]=[CH:28]3)=[O:21])=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[N:4]([C:16]2[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]3[CH:24]=[CH:25][CH:26]=[C:27]4[C:32]=3[N:31]=[CH:30][CH:29]=[CH:28]4)=[O:21])=[CH:18][CH:17]=2)[CH:3]1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 41661718HCID 41661718, compoundHCID 89814013HCID 89814013, compound

Product 1

HCID 89814176HCID 89814176, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A microwave vial was charged with 5,5-dimethyl-4-(pyridin-3-yl)oxazolidin-2-one (0.072 g, 0.376 mmol), 4-iodo-N-(quinolin-8-yl)benzamide (0.155 g, 0.414 mmol), tribasic potassium phosphate (0.399 g, 1.880 mmol) and dioxane (3.50 mL). The mixture was purged with argon and then copper (I) iodide (0.072 g, 0.376 mmol) and N,N′-dimethylethylenediamine (0.081 mL, 0.752 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 1 hour in a microwave. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford an orange brown solid. This residual material was purified by column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (+/−)-(R/S)-4-(5,5-dimethyl-2-oxo-4-(pyridin-3-yl)oxazolidin-3-yl)-N-(quinolin-8-yl)benzamide (0.092 g, 0.210 mmol, 56% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.98 (s, 3H), 1.69 (s, 3H), 5.69 (s, 1H), 7.40 (dd, J=8.02, 4.79 Hz, 1H), 7.57-7.79 (m, 6H), 7.90-8.04 (m, 2H), 8.45 (dd, J=8.31, 1.66 Hz, 1H), 8.54 (dd, J=4.74, 1.61 Hz, 1H), 8.60 (br. s., 1H), 8.67 (dd, J=7.63, 1.27 Hz, 1H), 8.95 (dd, J=4.25, 1.71 Hz, 1H), 10.56 (s, 1H). m/z (ESI) 439 (M+H)+.

Workup

  1. customThe mixture was purged with argon
  2. customThe system was purged with argon
  3. customthe tube was sealed
  4. filtrationThe reaction mixture was filtered through Celite® brand
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated
  7. customto afford an orange brown solid
  8. customThis residual material was purified by column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane)

Sources & evidence

ORD record
ord-6df449fef00e48759069e24e00ed6489
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…