Ethanol → 6-(3,5-dimethylisoxazol-4-yl)-4-(1-hydroxy-1-(pyridin-2-yl)propyl)-1H-benzo[d]imidazol-2(3H)-one

HRID 1773731Notes

Reaction equation

HRID 1773731 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)=[O:20])[C:10]3[N:14]=[C:13]([O:15]CC)[NH:12][C:11]=3[CH:18]=2)=[C:5]([CH3:27])[O:4][N:3]=1.[CH2:28]([Mg]Br)[CH3:29].CCO.Cl.O1CCOCC1>C1COCC1>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:19]([OH:20])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[CH2:28][CH3:29])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:18]=2)=[C:5]([CH3:27])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 117601753(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin 2-yl)methanoneHCID 178418443HCID 178418443, compound

Product 1

HCID 1176018176-(3,5-dimethylisoxazol-4-yl)-4-(1-hydroxy-1-(pyridin-2-yl)propyl)-1H-benzo[d]imidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(6-(3,5-dimethylisoxazol-4-yl)-2-ethoxy-1H-benzo[d]imidazol-4-yl)(pyridin-2-yl)methanone (20 mg, 0.055 mmol) was dissolved in dry THF (0.5 mL) and ethylmagnesium bromide (1.0 M, 0.27 mL, 0.27 mmol) was added dropwise. The reaction was allowed to stir at r.t. for 10 minutes and then a mixture of EtOH (1 mL) and 4.0M HCl/dioxane (0.5 mL) was added and the reaction was heated to 65° C. for 3 hours. The reaction was concentrated and purified by reverse-phase HPLC to afford the desired product as a white powder.

Workup

  1. additionwas added
  2. temperaturethe reaction was heated to 65° C. for 3 hours
  3. concentrationThe reaction was concentrated
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-7c81539e6ced4ba687e6ca740a9da30b
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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