1-Methylimidazole → HCID 131734984, compound

HRID 922742Notes

Reaction equation

HRID 922742 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[C:13]3([CH2:14][OH:15])[C:10]([CH3:16])([CH2:11][O:12]3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CN1C=CN=C1.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:13]3([CH2:14][O:15][S:38]([C:35]4[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=4)(=[O:40])=[O:39])[C:10]([CH3:16])([CH2:11][O:12]3)[CH2:9][CH2:8]2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86718260HCID 86718260, compound

Product 1

HCID 131734984HCID 131734984, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In 1 ml of toluene, 50 mg of Compound 8a-1 synthesized in Production Example 19 was dissolved. To the solution thus obtained, 39.5 μl of triethylamine, 22.2 μl of N-methylimidazole, and 53.6 mg of p-toluenesulfonyl chloride were added, and the resulting mixture was stirred at room temperature for 1.5 hours. After the reaction, water was added to the reaction solution thus obtained, and extraction with ethyl acetate was then carried out. The organic layer thus extracted was washed with an aqueous solution of hydrochloric acid, an aqueous solution of sodium hydrogen carbonate, and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 77.0 mg of Compound 9a-1-2.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. extractionextraction with ethyl acetate
  6. extractionThe organic layer thus extracted
  7. washwas washed with an aqueous solution of hydrochloric acid
  8. dry with materialan aqueous solution of sodium hydrogen carbonate, and saturated brine, and then dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled away
  10. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-334295b6828f459ea02f379755226c70
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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