N,N'-Dimethylethylenediamine → HCID 71736211, compound

HRID 525331Notes

Reaction equation

HRID 525331 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C:12]([CH3:14])([CH3:13])[O:11][C:10](=[O:15])[NH:9]2)=[CH:4][CH:3]=1.I[C:17]1[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[C:33]=2[N:32]=[CH:31][CH:30]=[CH:29]3)=[O:22])=[CH:19][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C:12]([CH3:13])([CH3:14])[O:11][C:10](=[O:15])[N:9]2[C:17]2[CH:35]=[CH:34][C:20]([C:21]([NH:23][C:24]3[CH:25]=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][CH:30]=[CH:29]4)=[O:22])=[CH:19][CH:18]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 41661718HCID 41661718, compoundHCID 89814018HCID 89814018, compound

Product 1

HCID 71736211HCID 71736211, compoundYield 89.1%

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 (S)-4-(4-fluorophenyl)-5,5-dimethyloxazolidin-2-one (0.050 g, 0.239 mmol), 4-iodo-N-(quinolin-8-yl)benzamide (0.098 g, 0.263 mmol), tribasic potassium phosphate (0.254 g, 1.195 mmol) and dioxane (2.50 mL). The mixture was purged with argon and then copper (I) iodide (0.046 g, 0.239 mmol) and N,N′-dimethylethylenediamine (0.051 mL, 0.478 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 2 hours in the microwave. The reaction mixture was filtered through Celite® brand filter aid, and the filtrate was concentrated to afford an orange brown solid. The residual material was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% EtOAc-hexane) to afford (S)-4-(4-(4-fluorophenyl)-5,5-dimethyl-2-oxooxazolidin-3-yl)-N-(quinolin-8-yl)benzamide (0.097 g, 0.213 mmol, 89% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95 (s, 3H) 1.66 (s, 3H) 5.60 (s, 1H) 7.16-7.29 (m, 2H) 7.36 (br. s., 2H) 7.58-7.81 (m, 5H) 7.97 (d, J=8.80 Hz, 2H) 8.45 (dd, J=8.31, 1.66 Hz, 1H) 8.67 (dd, J=7.68, 1.32 Hz, 1H) 8.95 (dd, J=4.21, 1.66 Hz, 1H) 10.55 (s, 1H). m/z (ESI) 456 (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. customThe residual material was purified

Sources & evidence

ORD record
ord-845f23ee1a26449e8410ec343fabf89e
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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