HCID 86701696, compound → HCID 178435673, compound

HRID 2174066Notes

Reaction equation

HRID 2174066 reaction equation
[CH2:1]([C:3]1[C:4]([CH:29]([OH:49])[C:30]2[N:34](COCC[Si](C)(C)C)[C:33]3[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:32]=3[N:31]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:7]=[C:6]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2].C(C1C(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=C2C1C=CC=CC=1)C>Cl.CO.CCOC(C)=O>[CH2:1]([C:3]1[C:4]([CH:29]([OH:49])[C:30]2[NH:34][C:33]3[CH:43]=[CH:44][C:45]([C:47]#[N:48])=[CH:46][C:32]=3[N:31]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([S:13]([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH:7]=[C:6]2[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:2]

Participants

6

Reactant 2

HCID 86701696HCID 86701696, compoundHCID 86701697HCID 86701697, compound

Product 1

HCID 178435673HCID 178435673, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of a mixture of (±)-2-((5-ethyl-7-methyl-3-phenyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and (±)-2-((5-ethyl-7-methyl-3-phenyl-1-tosyl-1H-indol-4-yl)(hydroxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (25 mg, 0.036 mmol) in 1M HCl in MeOH (2 mL) was stirred at 60° C. for 17 h. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with EtOAc. The mixture was successively washed by 5% aq. NaHCO3, H2O and brine, dried over Na2SO4, and filtered. Concentration of the filtrate gave the title compound, which was used in the next reaction without any further purification. MS (ESI+) m/z 561.2 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was successively washed by 5% aq. NaHCO3, H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-76bc9f86d85740719634b7daf429df12
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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