Trifluoroacetic acid → HCID 178466031, compound

HRID 2064599Notes

Reaction equation

HRID 2064599 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-6a46b9370d8d484c807fe478eefce39f
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

Loading…