Hydrochloric Acid → [4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenyl]-(4-fluoro-phen yl)-amine

HRID 532545Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

(4-Fluoro-phenyl)-{4-[4-(2-trimethylsilanyl-ethoxymethyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl]-phenyl}-amine (0.25 g, 0.5 mmol) was dissolved in MeOH and treated with concentrated HCl (0.16 mL, 5 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 [4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenyl]-(4-fluoro-phen yl)-amine (0.14 g, 0.42 mmol) as white solid in 85% 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-94318b79311c405ea93eaeeeb4b4c792
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853207B2

Reaction notes

Loading…