Methyl iodide → HCID 58968622, compound

HRID 2075043Notes

Reaction equation

HRID 2075043 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH3:25])=[CH:17][C:16]=1[CH:26]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[OH:27])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[H-].[Na+].[CH3:45]I>C1COCC1>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[C:18]([CH3:25])=[CH:17][C:16]=1[CH:26]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[O:27][CH3:45])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58968744HCID 58968744, compound

Product 1

HCID 58968622HCID 58968622, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-5-methyl-4-trifluoromethyl-phenyl)-cyclohexyl-methanol (8 mg, 0.01 mmol) in THF (0.15 mL) at 0° C. was added sodium hydride (4.2 mg, 0.11 mmol). The mixture was stirred at room temperature for 30 minutes. Methyl iodide (10 μL, 0.2 mmol) was added at 0° C. The mixture was stirred at room temperature overnight. The mixture was quenched with methanol and purified by chromatography over 12+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound (3.6 mg, 40%). 1H NMR (400 MHz, CDCl3) δ ppm 0.92-1.20 (m, 6H) 1.41-1.51 (m, 1H) 1.61 (d, J=8.71 Hz, 2H) 1.67-1.74 (m, 1H) 1.93 (d, J=11.62 Hz, 1H) 2.46 (s, 3H) 3.04 (s, 3H) 4.04 (d, J=7.05 Hz, 1H) 4.21 (s, 3H) 4.63-4.72 (m, 3H) 4.84 (d, J=16.18 Hz, 1H) 7.27 (s, 1H) 7.30 (s, 1H) 7.63 (s, 2H) 7.77 (s, 1H). MS (ES30) Calc: 623.2, Found: 624.6 (M+1) According to the procedure described in example 23 and using the corresponding aryl bromide and aldehyde reagent, example 24 was prepared.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with methanol
  3. custompurified by chromatography over 12+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-217b25ceb44b43f7999a86645034a459
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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