Magnesium → HCID 178512072, compound

HRID 1972233Notes

Reaction equation

HRID 1972233 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[CH2:16][N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:38][C:39]#[N:40])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[Mg]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=4)[CH2:16][NH:15][C:14]3=[N:38][C:39]#[N:40])=[CH:11][CH:12]=2)=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 5462224MagnesiumHCID 86645371HCID 86645371, compound

Product 1

HCID 178512072HCID 178512072, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)—N-(3-(4-(4-chlorophenoxy)phenyl)-1-tosyl-4-(3-(trifluoromethyl)-phenyl)imidazolidin-2-ylidene)cyanamide (1.06 g, 1.73 mmol) in MeOH (17 mL) is added magnesium powder (0.42 g, 17.3 mmol). The reaction mixture is heated to reflux for 45 min. After cooling down to room temperature, the mixture is quenched with saturated NH4Cl aqueous solution (150 mL) and extracted with EtOAc (3×75 mL). The combined organic layer is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography (20˜70% EtOAc/Hexanes) to provide the title compound (0.62 g, 78% yield) as a white solid product; 1H NMR (CDCl3, 400 MHz) δ 7.60 (m, 1H), 7.51 (m, 3H), 7.27 (d, 2H), 7.15 (d, 2H), 6.88 (m, 4H), 6.65 (br, 1H), 5.40 (dd, 1H), 4.21 (t, 1H), 3.63 (dd, 1H); HPLC-MS calculated for C23H16ClF3N4O (M+H+) 457.1, found 457.1.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 45 min
  3. customthe mixture is quenched with saturated NH4Cl aqueous solution (150 mL)
  4. extractionextracted with EtOAc (3×75 mL)
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (20˜70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-f742038186fd4bd3a153c1b0a83dd256
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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