Methyl iodide → HCID 58031591, compound

HRID 560917Notes

Reaction equation

HRID 560917 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[N:14]([C:17]3[S:18][C:19]([C:23]([NH:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:24])=[C:20]([CH3:22])[N:21]=3)[CH:13]=[N:12]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:36]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15](=[O:16])[N:14]([C:17]3[S:18][C:19]([C:23]([N:25]([CH3:36])[CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[O:24])=[C:20]([CH3:22])[N:21]=3)[CH:13]=[N:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59481241HCID 59481241, compound

Product 1

HCID 58031591HCID 58031591, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(1-(2-(4-fluorophenylamino)ethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (0.10 g, 0.40 mmol) in anhydrous tetrahydrofuran (10 mL) was treated with sodium hydride (60% suspension in mineral oil, 0.02 g, 0.47 mmol) at ambient temperature for 30 minutes, followed by the addition of iodomethane (0.015 mL, 0.24 mmol). The reaction mixture was stirred at ambient temperature for 1 hour, quenched with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate to afford the title compound as a white solid in 25% yield (0.03 g): 1H NMR (300 MHz, CDCl3) δ 8.60-8.49 (m, 2H), 8.24 (s, 1H), 7.69-7.59 (m, 1H), 7.35-7.27 (m, 1H), 6.91-6.77 (m, 2H), 6.59-6.49 (m, 2H), 4.69 (s, 2H), 4.15-4.04 (m, 2H), 3.99-3.87 (m, 1H), 3.54-3.44 (m, 2H), 2.98 (s, 3H), 2.39 (s, 3H); MS (ES+) m/z 468.18 (M+1).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-d0e597f00c964c71a089736415c3bc78
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

Loading…