Water → HCID 66879692, compound

HRID 1294521Notes

Reaction equation

HRID 1294521 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:27])[N:13]([C:15]3[N:20]=[C:19]([N:21]4[CH2:26][CH2:25][S:24][CH2:23][CH2:22]4)[CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[OH2:28].C(=O)(O)[O-:30].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:27])[N:13]([C:15]3[N:20]=[C:19]([N:21]4[CH2:22][CH2:23][S:24](=[O:30])(=[O:28])[CH2:25][CH2:26]4)[CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11165348HCID 11165348, compound

Product 1

HCID 66879692HCID 66879692, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-{6-[4-(3-Chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridin-2-yl}-thiomorpholine (250 mg, 0.63 mmol) was dissolved in 6 mL of methanol and Oxone monopersulfate triple salt (389 mg, 0.63 mmol) was added. The reaction mixture was stirred at room temperature for 4 days. Then additional Oxone monopersulfate triple salt (78 mg, 1.3 mmol) was added to drive the reaction to completion. The reaction mixture was treated with 50 mL water. The pH was adjusted to 9 by addition of sat. sodium bicarbonate solution, and the reaction mixture was extracted three times with methylene chloride (50 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography (heptane/ethyl acetate 1:4) and the desired product was obtained as a white solid (97 mg, 36%), MS: m/e=427.4, 429.4 (M+H+).

Workup

  1. customthe reaction to completion
  2. extractionthe reaction mixture was extracted three times with methylene chloride (50 mL each)
  3. dry with materialThe combined organic extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material was purified by flash chromatography (heptane/ethyl acetate 1:4)

Sources & evidence

ORD record
ord-e73a174d63d94c7f9116b8238c68fccc
Source dataset
uspto-grants-2007_07
Patent number
US07241760B2

Reaction notes

Loading…