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

HRID 532640Notes

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:25]=[CH:24][N:23]=[CH:22][CH:21]=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]=[CH:22][N:23]=[CH:24][CH:25]=5)=[CH:18][C:19]=4[C:12]=3[NH:11][N:10]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-(4-Methoxy-phenyl)-2-pyridin-4-yl-4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.49 g, 0.98 mmol) was dissolved in MeOH and treated with concentrated HCl (0.3 mL, 9.4 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-pyridin-4-yl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pent alene (0.35 g, 0.95 mmol) as brown solid in 98% yield.

Workup

temperatureThe solution was cooled to room temperature
filtrationthe resultant precipitate was filtered
washwashed with MeOH
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-439d0250e44a4a55a23f70a08e0187f4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

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