1-Cyclopropyl-butane-1,3-dione → HCID 11667437, compound

HRID 133542Notes

Reaction equation

[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[CH:19]1([C:22](=[O:27])[CH2:23][C:24](=O)[CH3:25])[CH2:21][CH2:20]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:19]1([C:22]([C:23]2[C:24]([CH3:25])=[N:1][C:2]3[S:10][C:5]4[CH2:6][O:7][CH2:8][CH2:9][C:4]=4[C:3]=3[C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:27])[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 100 mg (0.38 mmol) (2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-yl)-phenyl-methanone in 5 ml acetic acid was added 73 mg (0.57 mmol) of 1-cyclopropyl-butane-1,3-dione (prep. described in the patent DE 94-4404059) and one drop of sulfuric acid. The mixture was then stirred at 70° C. for 2 hours and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 3:1) afforded 50 mg (37%) cyclopropyl-(2-methyl-4-phenyl-5,8-dihydro-6H-7-oxa-9-thia-1-aza-fluoren-3-yl)-methanone as a yellow solid. ES-MS m/e (%): 350 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9c8adc1cd5794214b4a6aa252ca90d0c
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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