HCID 86701702, compound → HCID 178427339, compound

HRID 2174071Notes

Reaction equation

HRID 2174071 reaction equation
[CH3:1][C:2]1[C:3]([CH:35]([OH:55])[C:36]2[N:40](COCC[Si](C)(C)C)[C:39]3[CH:49]=[CH:50][C:51]([C:53]#[N:54])=[CH:52][C:38]=3[N:37]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[C:5]2[C:22]1[N:26](COCC[Si](C)(C)C)[N:25]=[CH:24][CH:23]=1.CC1C(C(O)C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2C1N(COCC[Si](C)(C)C)N=CC=1>Cl.CO.C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH:35]([OH:55])[C:36]2[NH:40][C:39]3[CH:49]=[CH:50][C:51]([C:53]#[N:54])=[CH:52][C:38]=3[N:37]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:19])=[CH:20][CH:21]=1)(=[O:14])=[O:13])[CH:6]=[C:5]2[C:22]1[NH:26][N:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 86701702HCID 86701702, compoundHCID 86701703HCID 86701703, compound

Product 1

HCID 178427339HCID 178427339, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of a mixture of (±)-2-((5,7-dimethyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5,7-dimethyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (250 mg, 0.314 mmol) in 1M HCl in MeOH (2 mL) was stirred at 60° C. for 16 h. The reaction mixture was cooled to room temperature, and diluted with CH2Cl2. The layers were separated and the organic layer was washed with 5% aq. NaHCO3, H2O, and brine, dried over Na2SO4, and filtered. After concentration of the filtrate, the resulting residue was purified by silica gel flash column chromatography [CH2Cl2/(2M NH3 in MeOH)=94/6 then 93/7] to give the title compound. MS (ESI+) m/z 537.1 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with 5% aq. NaHCO3, H2O, and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customAfter concentration of the filtrate, the resulting residue was purified by silica gel flash column chromatography [CH2Cl2/(2M NH3 in MeOH)=94/6

Sources & evidence

ORD record
ord-73e8c93a4ac54f6385edc47523d1da18
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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