Hydrochloric Acid → HCID 178503093, compound

HRID 2064589Notes

Reaction equation

HRID 2064589 reaction equation
[CH3:1][C:2]1[C:25]([CH3:26])=[CH:24][C:5]2[N:6](COCC[Si](C)(C)C)[C:7]([C:9]3[CH:13]=[C:12]([S:14][CH3:15])[NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:26][C:25]1[C:2]([CH3:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[CH:13]=[C:12]([S:14][CH3:15])[NH:11][N:10]=3)=[N:6][C:5]=2[CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178503092HCID 178503092, compound

Product 1

HCID 178503093HCID 178503093, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5,6-dimethyl-2-(5-methylsulfanyl-1H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole [90 mg, Reference Example 1(a)], hydrochloric acid (2 mL, 4N) and ethanol (4 mL) was heated at reflux temperature for 16 hours then cooled to room temperature. The pH of the reaction mixture was adjusted to 7 by addition of saturated sodium bicarbonate solution. The resulting solid was filtered, then washed with water and then dried in a vacuum oven to give 5,6-dimethyl-2-(5-methylsulfanyl-1H-pyrazol-3-yl)-1H-benzoimidazole (38 mg). LC-MS (METHOD A): RT=2.22 minutes; 259 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6d805df29a3d45f2b6d5995d0d2baf12
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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