Hydrochloric Acid → 6-(4-Methoxy-phenyl)-2-(6-methoxy-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532661Notes

Reaction equation

HRID 532661 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH2:14][C:15]4[S:16][C:17]([C:20]5[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=5)=[CH:18][C:19]=4[C:12]=3[N:11](COCC[Si](C)(C)C)[N:10]=2)=[CH:5][CH:4]=1.Cl>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]3[CH2:14][C:15]4[S:16][C:17]([C:20]5[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=5)=[CH:18][C:19]=4[C:12]=3[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866992416-(4-Methoxy-phenyl)-2-(6-methoxy-pyridin-3-yl)-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Product 1

HCID 866992426-(4-Methoxy-phenyl)-2-(6-methoxy-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(4-Methoxy-phenyl)-2-(6-methoxy-pyridin-3-yl)-4-(2-trimethylsilan yl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.35 g, 0.69 mmol) was dissolved in MeOH and treated with concentrated HCl (0.21 mL, 6.9 mmol). The reaction mixture was heated at 100° C. for 4 hr. The solution was cooled to room temperature and the resultant precipitate was filtered, washed with MeOH and concentrated under reduced pressure to provide the corresponding 6-(4-Methoxy-phenyl)-2-(6-methoxy-pyridin-3-yl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.55 g, 0.6 mmol) as white solid in 87% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with MeOH
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2526f7fb5cd44b0b4976a26e2da2bab
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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