Methanol → N-Benzyl-4-methyl-2-(2-oxo-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamide

HRID 45384Notes

Reaction equation

HRID 45384 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([O:24]C)[CH:19]=2)=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[Si](C)(C)C.CO>C(Cl)(Cl)Cl>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:17]([C:18]2[CH:23]=[CH:22][NH:21][C:20](=[O:24])[CH:19]=2)=[O:26])=[N:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 59369644HCID 59369644, compound

Product 1

HCID 59369671N-Benzyl-4-methyl-2-(2-oxo-1,2-dihydropyridine-4-carboxamido)thiazole-5-carboxamideYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-benzyl-2-(2-methoxyisonicotinamido)-4-methylthiazole-5-carboxamide (0.26 g, 0.68 mmol) in anhydrous chloroform (15 mL) was added iodotrimethylsilane (1.37 g, 6.80 mmol) at 0° C. The mixture was refluxed for 16 hours and cooled down to ambient temperature. Methanol (3 mL) was added dropwise to quench the reaction. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated sodium bicarbonate solution (2×100 mL), and brine (150 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrate in vacuo. The residue was recrystallized from ethyl acetate and methanol to yield a colorless solid in 55% yield (0.13 g); m.p. 290-292° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.74 (s, br, 2H), 8.63 (t, J=5.9 Hz, 1H), 7.48 (d, J=6.8 Hz, 1H), 7.35-7.17 (m, 5H), 6.95 (d, J=1.6 Hz, 1H), 6.66 (dd, J=1.6, 6.8 Hz, 1H), 4.37 (d, J=5.9 Hz, 2H), 2.49 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 165.5, 162.6, 163.1, 162.0, 144.1, 140.0, 136.8, 128.7, 127.6, 127.1, 120.3, 119.2, 103.3, 43.0, 17.0; MS (ES+) m/z 369.2 (M+1).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. customto quench
  3. customthe reaction
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. washwashed with saturated sodium bicarbonate solution (2×100 mL), and brine (150 mL)
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrate in vacuo
  10. customThe residue was recrystallized from ethyl acetate and methanol
  11. customto yield a colorless solid in 55% yield (0.13 g)

Sources & evidence

ORD record
ord-d649733dfd09497fbb0652797e6c0d9a
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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