Methyl iodide → HCID 66634531, compound

HRID 1911968Notes

Reaction equation

HRID 1911968 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([N:13]([CH3:21])[C:14]([NH:16][CH2:17][CH2:18][S:19][CH3:20])=[O:15])=[N:10][N:9]=2)[CH:5]=[N:6][CH:7]=1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([N:13]([CH3:21])[C:14]([N:16]([CH3:25])[CH2:17][CH2:18][S:19][CH3:20])=[O:15])=[N:10][N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66614303HCID 66614303, compound

Product 1

HCID 66634531HCID 66634531, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

An ice-cold solution of 1-[5-(5-fluoro-pyridin-3-yl)-[1,3,4]thiadiazol-2-yl]-1-methyl-3-(2-methylsulfanyl-ethyl)-urea (0.132 g, 0.4 mmol) in N,N-dimethylformamide (0.6 mL) was treated with sodium hydride (60% in mineral oil, 0.018 g, 0.4 mmol) and stirred for 5 minutes before addition of a solution of iodomethane (0.063 g, 0.4 mmol) in N,N-dimethylformamide (0.1 mL). The ice bath was removed after 5 minutes. The reaction mixture was stirred at room temperature for 14 hours, diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over MgSO4, purified by normal and reversed phase chromatography to give the title compound as a colorless gum (0.027 g, 20%): IR (KBr thin film) 1658 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.53 (d, J=3.2 Hz, 1H), 8.02 (ddd, J=9.1, 4.5, 1.7 Hz, 1H), 3.66 (s, 3H), 3.59 (t, J=6.8 Hz, 2H), 3.06 (s, 3H), 2.78 (t, J=7.1 Hz, 2H), 2.14 (s, 3H); ESIMS m/z 342 ([M+H]+).

Workup

  1. customThe ice bath was removed after 5 minutes
  2. additiondiluted with water (30 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe combined organic extracts were washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. custompurified by normal and reversed phase chromatography

Sources & evidence

ORD record
ord-33c407eba2d44e75b20f4503c9dbd6bf
Source dataset
uspto-grants-2013_12
Patent number
US08604211B2

Reaction notes

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