Hydrochloric Acid → HCID 178470773, compound

HRID 2174037Notes

Reaction equation

HRID 2174037 reaction equation
Cl.O1CCOCC1.[C:8]([C:10]1[CH:53]=[CH:52][C:13]2[N:14](COCC[Si](C)(C)C)[C:15]([CH:17]([C:23]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[C:28]4[C:24]=3[CH:25]=[CH:26][N:27]4[S:34]([C:37]3[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=3)(=[O:36])=[O:35])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:16][C:12]=2[CH:11]=1)#[N:9].C(C1C=CC2N=C(C(C3C(C)=CC(C)=C4C=3C=CN4S(C3C=CC(C)=CC=3)(=O)=O)C(OCC)=O)N(COCC[Si](C)(C)C)C=2C=1)#N>CCO>[C:8]([C:10]1[CH:53]=[CH:52][C:13]2[NH:14][C:15]([CH:17]([C:23]3[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[C:28]4[C:24]=3[CH:25]=[CH:26][N:27]4[S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=3)(=[O:36])=[O:35])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:16][C:12]=2[CH:11]=1)#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86701658HCID 86701658, compoundHCID 86701659HCID 86701659, compound

Product 1

HCID 178470773HCID 178470773, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

HCl in dioxane (4 M, 2.28 mL, 9.13 mmol) was added to a solution of a mixture of (±)-ethyl 2-(5-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)acetate and (±)-ethyl 2-(6-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2-yl)-2-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)acetate (600 mg, 0.913 mmol) in EtOH (12 mL) at room temperature. The resulting mixture was stirred at 60° C. overnight then partitioned between EtOAc and sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc. The combined organics were washed with brine, dried, and concentrated to give the title compound. The residue was taken onto the next step without further purification. MS (ESI+) m/z 527.3 (M+H).

Workup

  1. customthen partitioned between EtOAc and sat. aq. NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organics were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0f5aff4beffe4e56b797f1738fb7acb3
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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