Sodium Bicarbonate → HCID 178435786, compound

HRID 2174026Notes

Reaction equation

HRID 2174026 reaction equation
[C:1]([C:3]1[CH:49]=[CH:48][C:6]2[N:7](COCC[Si](C)(C)C)[C:8]([CH:10]([C:18]3[C:26]([CH2:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[NH:11]S(C(C)(C)C)=O)=[N:9][C:5]=2[CH:4]=1)#[N:2].C(C1C=CC2N=C(C(C3C(CC)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)NS(C(C)(C)C)=O)N(COCC[Si](C)(C)C)C=2C=1)#N.C([O-])(O)=O.[Na+]>Cl.CO>[NH2:11][CH:10]([C:18]1[C:26]([CH2:27][CH3:28])=[CH:25][C:24]([CH3:29])=[C:23]2[C:19]=1[CH:20]=[CH:21][N:22]2[S:30]([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31])[C:8]1[NH:7][C:6]2[CH:48]=[CH:49][C:3]([C:1]#[N:2])=[CH:4][C:5]=2[N:9]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 86701630HCID 86701630, compoundHCID 86701631HCID 86701631, compound

Product 1

HCID 178435786HCID 178435786, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of a mixture of (±)-N-((5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)methyl)-2-methylpropane-2-sulfinamide and (±)-N-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(5-ethyl-7-methyl-1-tosyl-1H-indol-4-yl)methyl)-2-methylpropane-2-sulfinamide (574 mg, 0.8 mmol) in 1M HCl in MeOH (10 mL) was stirred at room temperature for 1.5 h, and then at 60° C. for 18 h. The reaction mixture was basified by 5% aq. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2. The organic phase was successively washed with H2O and brine, dried over Na2SO4, and filtered. After concentration the residue was purified by silica gel flash column chromatography (heptanes/EtOAc=1/1 to 0/1) to give the title compound. MS (ESI+) m/z 484.2 (M+H).

Workup

  1. waitat 60° C. for 18 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe organic phase was successively washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationAfter concentration the residue
  8. customwas purified by silica gel flash column chromatography (heptanes/EtOAc=1/1 to 0/1)

Sources & evidence

ORD record
ord-67fd518e492349019d045fe109aad0f9
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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