Triethylamine → HCID 23725534, compound

HRID 2219423Notes

Reaction equation

HRID 2219423 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]([CH2:27]O)[N:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:17]=1.C(N(CC)CC)C.CS([Cl:40])(=O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:40][CH2:27][C:15]1[N:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH:17]=[C:13]([C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])[N:14]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 23725533HCID 23725533, compound

Product 1

HCID 23725534HCID 23725534, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(5-methyl-3-phenyl-isoxazol-4-yl)-1-(4-nitro-phenyl)-1H-imidazol-2-yl]-methanol (50 mg, 0.13 mmol) in DCM (5 mL) at 0° C. was added triethylamine (92.6 μL, 0.66 mmol) and methanesulfonyl chloride (30.97 μL, 0.40 mmol) and the resulting mixture allowed to warm up to room temperature over 3 h and then stirred for a subsequent 2 h. The mixture was then poured onto a saturated solution of sodium hydrogen carbonate and extracted with DCM. The combined organic layers were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (37 mg, 70%) which was obtained as a yellow foam. MS: m/e=395.0 [M+H]+.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were then dried over sodium sulphate
  3. customevaporated
  4. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-8750235449cb47de9bedfb600ce235ba
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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