HCID 86701687, compound → HCID 178437481, compound

HRID 2174061Notes

Reaction equation

[CH2:1]([C:3]1[C:4]([C:23]([C:25]2[N:29](COCC[Si](C)(C)C)[C:28]3[CH:38]=[CH:39][C:40]([C:42]#[N:43])=[CH:41][C:27]=3[N:26]=2)=[CH2:24])=[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]=[CH:6]2)[CH3:2].C(C1C(C(C2N(COCC[Si](C)(C)C)C3C=C(C#N)C=CC=3N=2)=C)=C2C(=C(C)C=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2)C>Cl.CO.C(Cl)Cl>[CH2:1]([C:3]1[C:4]([C:23]([C:25]2[NH:29][C:28]3[CH:38]=[CH:39][C:40]([C:42]#[N:43])=[CH:41][C:27]=3[N:26]=2)=[CH2:24])=[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]=[CH:6]2)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of a mixture of 2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and 2-(1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (100 mg, 0.164 mmol) in 1M HCl in MeOH (10 mL) was stirred at 60° C. for 5 h. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with CH2Cl2. The layers were separated and the organic phase was successively washed with 5% aq. NaHCO3, H2O and brine, dried over Na2SO4, and filtered. Concentration of the filtrate gave the title compound, without need of any further purification. MS (ESI+) m/z 481.2 (M+H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe layers were separated
washthe organic phase was successively washed with 5% aq. NaHCO3, H2O and brine
dry with materialdried over Na2SO4
filtrationfiltered

Sources & evidence

ORD record: ord-9952122de84045fc92410c312f3aea35
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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