Hydrochloric Acid → HCID 178503112, compound

HRID 2173927Notes

Reaction equation

HRID 2173927 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([CH:11]([C:19]3[C:27]([S:28][CH3:29])=[CH:26][C:25]([CH3:30])=[C:24]4[C:20]=3[CH:21]=[CH:22][N:23]4[S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[NH:12]S(C(C)(C)C)=O)[N:8](COCC[Si](C)(C)C)[C:7]=2[CH:49]=1)#[N:2].C(C1C=CC2N(COCC[Si](C)(C)C)C(C(C3C(SC)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)NS(C(C)(C)C)=O)=NC=2C=1)#N.Cl.CO>>[NH2:12][CH:11]([C:19]1[C:27]([S:28][CH3:29])=[CH:26][C:25]([CH3:30])=[C:24]2[C:20]=1[CH:21]=[CH:22][N:23]2[S:31]([C:34]1[CH:35]=[CH:36][C:37]([CH3:38])=[CH:39][CH:40]=1)(=[O:33])=[O:32])[C:9]1[NH:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:49][C:7]=2[N:8]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86701477HCID 86701477, compoundHCID 86701478HCID 86701478, compound

Product 1

HCID 178503112HCID 178503112, compound

Conditions

Temperature
60 °C

Procedure

To a solution of a mixture of (±)-N-((6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)methyl)-2-methylpropane-2-sulfinamide and (±)-N-((5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)(7-methyl-5-(methylthio)-1-tosyl-1H-indol-4-yl)methyl)-2-methylpropane-2-sulfinamide (1 g, 1.36 mmol), HCl in methanol (1.25 M) (22 mL, 27 mmol) was added and the reaction stirred at 60° C. for 2 h. The reaction was then evaporated, basified with NH4OH (33% NH3 in H2O) and extracted with EtOAc. The organic extract was dried over MgSO4 filtered and concentrated to give the title compound without the need for further purification. MS (ESI+) m/z 502.2 (M+H).

Workup

  1. additionwas added
  2. customThe reaction was then evaporated
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40868b6d9931450bb16ce8afafa88482
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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