Triethylamine → HCID 68663088, compound

HRID 452822Notes

Reaction equation

HRID 452822 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[CH:13][N:12]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[C:11]=3[CH:21]=2)=[N:4][N:3]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[CH:13][N:12]([CH:15]4[CH2:20][CH2:19][N:18]([S:30]([CH3:29])(=[O:32])=[O:31])[CH2:17][CH2:16]4)[C:11]=3[CH:21]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68663831HCID 68663831, compound

Product 1

HCID 68663088HCID 68663088, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(5-methyl-1,3,4-oxadiazol-2-yl)-1-(4-piperidinyl)-1H-benzimidazole (0.25 g, 0.88 mmol) and triethylamine (0.24 mL, 1.76 mmol) in tetrahydrofuran (5 mL) was added methanesulfonyl chloride (0.10 mL, 1.32 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 1 hr. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=1/0-19/1) and recrystallized from diethyl ether/methanol to give the title compound (0.19 g, yield 60%) as colorless crystals.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/methanol=1/0-19/1)
  4. customrecrystallized from diethyl ether/methanol

Sources & evidence

ORD record
ord-e06d6bb2eb144eae8d2a10098d8a7fe2
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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