Acetone → HCID 178454825, compound

HRID 2389481Notes

Reaction equation

HRID 2389481 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.Cl[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][N:23](C(=O)CCC)[CH2:22]1.[C:32]([O-:35])([O-])=O.[K+].[K+].[CH3:38][C:39]([CH3:41])=O>>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[SH:1]([CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][NH:23][CH2:22]1)[C:32](=[O:35])[CH2:38][CH2:39][CH3:41])([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 63393068HCID 63393068, compoundHCID 178451223HCID 178451223, compound

Product 1

HCID 178454825HCID 178454825, compound

Procedure

A suspension of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Precursor 3-I, 1 g, 3.79 mmol), 1-(3-chloromethyl-piperidin-1-yl)-butan-1-one (alkylating agent I-01d, 771 mg, 3.79 mmol) and K2CO3 (1.05 g, 7.58 mmol) in acetone (10 ml) is refluxed for 36 h. The crude mixture is filtered over a fritted-funnel and the solvent evaporated in vacuo. The resulting brown gum is purificated by column chromatography on silica-gel (AcOEt/heptane, 3:7 to 1:1), yielding the title compound (802 mg) in 49% as a colourless oil: tR=2.19 min (LC-1), ESI-MS (pos.): m/z 432.24 [M+H]+.

Workup

  1. temperatureis refluxed for 36 h
  2. filtrationThe crude mixture is filtered over a fritted-funnel
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-98576d7521684e44b95bfbf6426f08ff
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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