p-Toluenesulfonic acid → HCID 59564416, compound

HRID 2096263Notes

Reaction equation

HRID 2096263 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:31])[CH2:23][N:24]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[N:25]2)[CH2:18][CH2:17]1.ClC(Cl)C.CC1C=CC(S(O)(=O)=O)=CC=1>>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[CH2:21][CH2:20][N:19]([C:22](=[O:31])[CH2:23][N:24]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[N:25]2)[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 63651,1-DichloroethaneHCID 59548846HCID 59548846, compound

Product 1

HCID 59564416HCID 59564416, compoundYield 89.4%

Conditions

Temperature
130 °C

Procedure

The N-(2-amino-phenyl)-2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzamide (0.050 g, 0.116 mmol) is dissolved into 2 mL of dichloroethane and placed in a microwave tube. To this is added a catalytic amt. of p-TsOH. The mixture is heated in a microwave at 130° C. for 20 min and then 160° C. for 30 min. The reaction mixture is concentrated to dryness and the product is purified using a Gilson Prep HPLC system eluting with 20%-100% CH3CN/H2O) to give 43 mg of desired product. Impure fractions are concentrated and purified using a SiO2 prep plate eluting with (5% MeOH/CH2Cl2) to give an additional 17.5 mg of 1-{4-[2-(1H-benzoimidazol-2-yl)-phenyl]-piperazin-1-yl}-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone.

Workup

  1. customplaced in a microwave tube
  2. additionTo this is added a catalytic amt
  3. concentrationThe reaction mixture is concentrated to dryness
  4. customthe product is purified
  5. washeluting with 20%-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-1cc6124ad1184e5087b7ea832a31974e
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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