1-(methoxymethyl)-1H-imidazole → HCID 22042653, compound

HRID 2053666Notes

Reaction equation

HRID 2053666 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.C([Li])CCC.[CH3:14][N:15]([C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C1COCC1>[CH3:14][N:15]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:36])([C:5]2[N:4]([CH2:3][O:2][CH3:1])[CH:8]=[CH:7][N:6]=2)[C:32]([F:34])([F:35])[F:33])=[CH:27][CH:26]=1)[S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 883591-(methoxymethyl)-1H-imidazoleHCID 22042580HCID 22042580, compoundHCID 178418339Butyllithium

Product 1

HCID 22042653HCID 22042653, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 55 mg (0.49 mmol) of 1-methoxymethyl-1H-imidazole in 5 ml of THF at −78° C. was added 0.20 ml (0.50 mmol) of a 2.5 M solution of n-butyllithium in hexanes and the resultant mixture was stirred at −78° C. for 30 mins. After this time, a solution of 160 mg (0.47 mmol) of N-methyl-N-(4-trifluoroacetyl-phenyl)benzenesulfonamide (Example 22, Step A) in 2 ml of THF was added and the resultant mixture stirred at −78° C. for a further 2 h, and then at room temperature for 14 h. After this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1) to give the title compound. 1H-NMR (CDCl3) δ 3.09 (s, 3H), 3.19 (s, 3H), 4.90 (s, 2H), 5.16 (brs, 1H), 7.07-7.16 (m, 4H), 7.42-7.62 (m, 7H). Mass Spectrum (CI+) m/e=456.1 (M+1).

Workup

  1. customAfter this time the reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography on silica gel (hexanes:EtOAc, 4:1)

Sources & evidence

ORD record
ord-7d6471fc32d545e0b7996e006bdf7572
Source dataset
uspto-grants-2008_02
Patent number
US07326812B2

Reaction notes

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