Trifluoroacetic acid → HCID 178466031, compound

HRID 2182357Notes

Reaction equation

HRID 2182357 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].C1(CNC([C:18]2[CH:35]=[CH:34][C:21]3[NH:22][C:23]([C:25]4[C:33]5[C:28](=CC=CC=5)[NH:27][N:26]=4)=[N:24][C:20]=3[CH:19]=2)=O)CCCCC1>>[CH2:3]([O:4][C:28]1[NH:27][N:26]=[C:25]([C:23]2[NH:22][C:21]3[CH:34]=[CH:35][CH:18]=[CH:19][C:20]=3[N:24]=2)[CH:33]=1)[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178522794HCID 178522794, compound

Product 1

HCID 178466031HCID 178466031, compound

Conditions

Temperature
50 °C

Procedure

A mixture of trifluoroacetic acid (6 mL) and 2-(5-ethoxy-1H-pyrazol-3-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (300 mg, Reference Example 11) was stirred at 50° C. for 1.5 hours. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and water (pH 10). The organic layer was dried and then evaporated. The residue was subjected to chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1, v/v) and then recrystallised from toluene to give 2-(5-ethoxy-1H-pyrazol-3-yl)-1H-benzoimidazole (0.1 g) as a colourless solid, mp 217-219.5° C. [Elemental analysis: C, 62.26%; H, 5.23%; N, 23.44%. Calculated for C12H12N4O: C, 63.15%; H, 5.30%; N, 24.55%].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water (pH 10)
  3. customThe organic layer was dried
  4. customevaporated
  5. additionThe residue was subjected to chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1
  6. customv/v) and then recrystallised from toluene

Sources & evidence

ORD record
ord-323c0b5aa1e44caf845fe89561e40b1c
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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