Methyl iodide → HCID 58968702, compound

HRID 2075031Notes

Reaction equation

HRID 2075031 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([OH:27])[CH3:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[H-].[Na+].[CH3:44]I>C1COCC1>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([O:27][CH3:44])[CH3:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58968621HCID 58968621, compound

Product 1

HCID 58968702HCID 58968702, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-1-cyclopentyl-ethanol (24.8 mg, 0.041 mmol) in THF (0.2 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 8 mg, 0.2 mmol). The mixture was stirred at room temperature for 30 minutes, cooled to 0° C. and methyl iodide (30 μL, 0.5 mmol) was added. The mixture was stirred at room temperature overnight. The reaction mixture was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexanes) to afford the title compound (17 mg, 67%). 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (t, J=8.09 Hz, 2H) 1.31-1.65 (m, 6H) 1.55 (s, 3H) 2.26-2.38 (m, 1H) 3.03 (s, 3H) 4.18 (s, 3H) 4.68-4.75 (m, J=16.18 Hz, 1H) 4.84 (d, J=16.18 Hz, 1H) 5.08 (d, J=17.84 Hz, 1H) 5.22 (d, J=17.43 Hz, 1H) 7.31 (d, J=8.71 Hz, 1H) 7.42-7.47 (m, 2H) 7.71 (s, 2H) 7.76 (s, 1H). MS (ES+) Calc: 609.2, Found: 610.5 (M+1).

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe mixture was stirred at room temperature overnight
  3. customThe reaction mixture was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-5bfe14cac448496296c454d2d99ea4fa
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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