Methyl iodide → HCID 58968678, compound

HRID 2075051Notes

Reaction equation

HRID 2075051 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=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]1([OH:29])[CH2:28][CH2:27][CH2:26]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[H-].[Na+].[CH3:41]I>C1COCC1>[F:38][C:2]([F:1])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=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]1([O:29][CH3:41])[CH2:26][CH2:27][CH2:28]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58968671HCID 58968671, compound

Product 1

HCID 58968678HCID 58968678, compoundYield 63.1%

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)-cyclobutanol (17.3 mg, 0.031 mmol) in THF (0.2 mL) at 0° C. was added sodium hydride (5 mg, 0.1 mmol). The mixture was stirred at room temperature for 30 minutes and methyl iodide (20 μL, 0.3 mmol) was added at 0° C. The mixture was stirred at room temperature overnight. Solvent was removed in vacuo. The residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexane) to afford the title compound (11.1 mg, 63%). 1H NMR (400 MHz, CDCl3) δ ppm 1.64-1.76 (m, 1H) 1.98-2.10 (m, 1H) 2.33-2.43 (m, 2H) 2.43-2.53 (m, 2H) 2.85 (s, 3H) 4.17-4.21 (m, 3H) 4.75 (s 2H) 4.86 (s, 2H) 7.41-7.46 (m, 2H) 7.50 (d, J=8.30 Hz, 1H) 7.73 (s, 2H) 7.76 (s, 1H). MS (ES+) Calc 567.2, Found: 568.4 (M+1) According to the procedure described in example 31 and using the corresponding ketone reagent, example 32 was prepared.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customSolvent was removed in vacuo
  3. customThe residue was purified by chromatography over 12+S Biotage silica column (eluted with 0-20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-53a0db77c2ad461e90cebe7f7e1a30e9
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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