Sodium Bicarbonate → HCID 178435784, compound

HRID 2174032Notes

Reaction equation

HRID 2174032 reaction equation
[C:1]([C:3]1[CH:50]=[CH:49][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([C:10]([NH:34]S(C(C)(C)C)=O)([C:12]3[C:20]([CH2:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH3:11])=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(NS(C(C)(C)C)=O)(C3C(CC)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)C)N(COCC[Si](C)(C)C)C=2C=1)#N.C([O-])(O)=O.[Na+]>Cl.CO>[NH2:34][C:10]([C:8]1[NH:7][C:6]2[CH:49]=[CH:50][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1)([C:12]1[C:20]([CH2:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[S:24]([C:27]1[CH:28]=[CH:29][C:30]([CH3:31])=[CH:32][CH:33]=1)(=[O:26])=[O:25])[CH3:11]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 86701645HCID 86701645, compoundHCID 86701646HCID 86701646, compound

Product 1

HCID 178435784HCID 178435784, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of (±)-N-(1-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)ethyl)-2-methylpropane-2-sulfinamide and (±)-N-(1-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-1-(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)ethyl)-2-methylpropane-2-sulfinamide (330 mg, 0.451 mmol) in 1M HCl in MeOH (5 mL) was stirred at 60° C. for 6 h. The reaction mixture was neutralized with 5% aq. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic phase was successively washed by H2O and brine, dried over Na2SO4, and filtered. After concentration, the residue was purified by silica gel flash column chromatography (CH2Cl2/EtOH=1/0 to 9/1) to give the title compound. MS (ESI−) m/z 496.4 (M−H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washThe organic phase was successively washed by H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationAfter concentration
  7. customthe residue was purified by silica gel flash column chromatography (CH2Cl2/EtOH=1/0 to 9/1)

Sources & evidence

ORD record
ord-c598caca8ac9454fa9ae18748265de26
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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