Potassium Hydroxide → HCID 178426456, compound

HRID 2173990Notes

Reaction equation

HRID 2173990 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]1[C:14]([CH2:33][C:34]2[NH:38][C:37]3[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:36]=3[N:35]=2)=[C:15]2[C:19](=[C:20]([CH3:22])[CH:21]=1)[N:18](S(C1C=CC(C)=CC=1)(=O)=O)[CH:17]=[CH:16]2.O.NN.[OH-].[K+]>CCO.C(Cl)Cl.FC(F)(F)CO>[NH2:3][CH2:12][C:13]1[C:14]([CH2:33][C:34]2[NH:38][C:37]3[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:36]=3[N:35]=2)=[C:15]2[C:19](=[C:20]([CH3:22])[CH:21]=1)[NH:18][CH:17]=[CH:16]2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 178427330HCID 178427330, compound

Product 1

HCID 178426456HCID 178426456, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 86701559HCID 86701559, compoundSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-((5-((1,3-dioxoisoindolin-2-yl)methyl)-7-methyl-1-tosyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (60 mg, 0.100 mmol) and hydrazine hydrate (5.01 mg, 0.100 mmol) in EtOH (2 mL) was stirred at 100° C. under microwave irradiation for 0.5 hr. To the mixture was added KOH (56.1 mg, 1.001 mmol), and then the mixture was stirred at 100° C. under the microwave irradiation for 1.75 h. The reaction mixture was diluted with CH2Cl2/2,2,2-trifluoroethanol (c.a. 9/1). The layers were separated and the organic layer was washed successively by H2O and brine, dried over Na2SO4, and filtered. After concentration, the residue was purified by silica gel flash column chromatography (CH2Cl2/2M NH3 in MeOH=94/6) to give the title compound. 1H NMR (400 MHz, DMSO-d6 with about 5 μL TFA) δ ppm 11.28 (br. s., 1H), 8.53 (br. s., 3H), 8.09 (s, 1H), 7.68 (d, J=8.34 Hz, 1H), 7.55 (dd, J=1.00, 8.30 Hz, 1H), 7.38 (t, J=2.80 Hz, 1H), 7.06 (s, 1H), 6.76-6.84 (m, 1H), 4.61 (s, 2H), 4.27-4.42 (m, 2H), 2.45 (s, 3H). HRMS calcd. for C19H17N6 (M+H)+ 316.1557. found 316.1559.

Workup

  1. stirringthe mixture was stirred at 100° C. under the microwave irradiation for 1.75 h
  2. customThe layers were separated
  3. washthe organic layer was washed successively by H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationAfter concentration
  7. customthe residue was purified by silica gel flash column chromatography (CH2Cl2/2M NH3 in MeOH=94/6)

Sources & evidence

ORD record
ord-218554cafb34491faf2e9019f656f450
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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