HCID 86701692, compound → HCID 178435674, compound

HRID 2174064Notes

Reaction equation

HRID 2174064 reaction equation
[CH2:1]([C:3]1[C:4]([CH2:36][C:37]2[N:41](COCC[Si](C)(C)C)[C:40]3[CH:50]=[CH:51][C:52]([C:54]#[N:55])=[CH:53][C:39]=3[N:38]=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[N:27](COCC[Si](C)(C)C)[N:26]=[CH:25][CH:24]=1)[CH3:2].C(C1C(CC2N(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)C>Cl.CO.C(Cl)Cl>[CH2:1]([C:3]1[C:4]([CH2:36][C:37]2[NH:41][C:40]3[CH:50]=[CH:51][C:52]([C:54]#[N:55])=[CH:53][C:39]=3[N:38]=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[NH:27][N:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

6

Reactant 2

HCID 86701692HCID 86701692, compoundHCID 86701693HCID 86701693, compound

Product 1

HCID 178435674HCID 178435674, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of a mixture of 2-((5-ethyl-7-methyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-5-carbonitrile and 2-((5-Ethyl-7-methyl-1-tosyl-3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)-1H-indol-4-yl)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole-6-carbonitrile (94 mg, 0.118 mmol) in 1M HCl in MeOH (5 mL) was stirred at 60° C. for 14 h. The reaction mixture was cooled to room temperature and 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 further purification. MS (ESI+) m/z 535.1 (M+H).

Workup

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

Sources & evidence

ORD record
ord-c5d3ef86742b4b2084c829f383bb130f
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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