Acetylacetone → 3-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester

HRID 133522Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[C:14]([C:18](=O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([NH2:17])[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27](=O)[CH2:28][C:29](=[O:31])[CH3:30]>C(O)(=O)C.S(=O)(=O)(O)O>[C:1]([O:5][C:6]([N:8]1[CH2:9][C:10]2[S:16][C:15]3[N:17]=[C:27]([CH3:26])[C:28]([C:29](=[O:31])[CH3:30])=[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:14]=3[C:11]=2[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 0.50 g (1.39 mmol) 2-amino-3-benzoyl-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester in 6 ml acetic acid was added 0.19 ml (1.89 mmol) of pentane-2,4-dione and two drops of sulfuric acid. The mixture was then stirred at 100° C. for 25 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 4:1) afforded 70 mg (12%) 3-acetyl-2-methyl-4-phenyl-5,8-dihydro-6H-9-thia-1,7-diaza-fluorene-7-carboxylic acid tert-butyl ester as a yellow oil. ES-MS m/e (%): 423 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-283e92c252444e2c9ae42f0e9638affb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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