Potassium Hydroxide → HCID 178437482, compound

HRID 2174062Notes

Reaction equation

HRID 2174062 reaction equation
[CH2:1]([C:3]1[C:4]([C:23]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([C:34]#[N:35])=[CH:33][C:27]=3[N:26]=2)=[CH2:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8](S(C1C=CC(C)=CC=1)(=O)=O)[CH:7]=[CH:6]2)[CH3:2].[OH-].[K+]>CCO.C(Cl)Cl.FC(F)(F)CO>[CH2:1]([C:3]1[C:4]([C:23]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][C:32]([C:34]#[N:35])=[CH:33][C:27]=3[N:26]=2)=[CH2:24])=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[CH:6]2)[CH3:2]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178437481HCID 178437481, compound

Product 1

HCID 178437482HCID 178437482, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 86701559HCID 86701559, compoundSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)vinyl)-1H-benzo[d]imidazole-5-carbonitrile (79 mg, 0.164 mmol) and KOH (46.1 mg, 0.822 mmol) in EtOH (3 mL) was stirred at 100° C. for 0.5 h under the microwave irradiation. The reaction mixture was diluted with CH2Cl2/2,2,2-trifluoroethanol (c.a. 9/1). The mixture was washed with H2O, dried over Na2SO4, and filtered and concentrated. The resulting residue was purified by RP-HPLC (HC-A), then (HC-B) to give the title compound. 1H NMR (400 MHz, DICHLOROMETHANE-d2 with about 5 μL TFA) δ ppm 8.46 (br. s., 1H), 8.04 (s, 1H), 7.86 (d, J=8.59 Hz, 1H), 7.73 (dd, J=1.14, 8.59 Hz, 1H), 7.37 (s, 1H), 7.27 (t, J=2.80 Hz, 1H), 7.07 (s, 1H), 6.25 (s, 2H), 2.47-2.65 (m, 5H), 1.14 (t, J=7.45 Hz, 3H). HRMS calcd. for C21H18N4 (M+H)+ 327.1610. found 327.1612.

Workup

  1. washThe mixture was washed with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by RP-HPLC (HC-A)

Sources & evidence

ORD record
ord-c2c8751876624f4b9f1ba5913b5e8e9a
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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