Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone → Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone

HRID 133540

Reaction equation

[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[CH2:12][NH:13][CH2:14][CH2:15][C:16]=4[C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:5])[CH2:3][CH2:2]1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[C:16]([C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[N:13][CH:12]=4)=[O:5])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 0.46 g (1.32 mmol) cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone in 7 ml diphenylethylene was added 230 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 35 mg (8%) cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone as a light yellow solid. ES-MS m/e (%): 345 (M+H+, 100).

Workup

additionpoured onto ethyl acetate (about 150 ml)
extractionextracted three times aqueous HCl (1M)
extractionthe product was extracted with ethyl acetate
dry with materialThe combined organic phase were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-aa59d649f886481b9711f5c1699912e0
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Linked notes

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