Hydrochloric Acid → HCID 178483310, compound

HRID 2174033Notes

Reaction equation

HRID 2174033 reaction equation
[C:1]([C:3]1[CH:51]=[CH:50][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([N:33](C)[C:34](=O)OC(C)(C)C)([C:12]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[S:23]([C:26]3[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH3:11])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(N(C)C(=O)OC(C)(C)C)(C3C(C)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)C)N(COCC[Si](C)(C)C)C=2C=1)#N.Cl.O1CCOCC1>CO.C([O-])([O-])=O.[Na+].[Na+].[Cl-].[Na+].O.CCOC(C)=O>[CH3:21][C:20]1[C:12]([C:10]([C:8]2[NH:7][C:6]3[CH:50]=[CH:51][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[N:9]=2)([NH:33][CH3:34])[CH3:11])=[C:13]2[C:17](=[C:18]([CH3:22])[CH:19]=1)[N:16]([S:23]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:15]=[CH:14]2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86701649HCID 86701649, compoundHCID 86701650HCID 86701650, compound

Product 1

HCID 178483310HCID 178483310, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (±)-tert-butyl 1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl(methyl)carbamate and (±)-tert-butyl 1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)ethyl(methyl)carbamate (95 mg, 0.130 mmol) in MeOH (326 μL) was mixed with 4 M HCl in dioxane (0.65 mL, 2.61 mmol) and the reaction stirred at 50° C. for 0.5 h. The reaction mixture was cooled to rt and diluted with 2 M aq. Na2CO3, brine and EtOAc. The products were extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60) to give the title compound. MS (ESI) m/z 496.34(M−1).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionThe products were extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel (heptane/EtOAc=100:0 to 40:60)

Sources & evidence

ORD record
ord-747decbb7dce4967bf1323f32111be84
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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