Acetylacetone → HCID 11603422, compound

HRID 133509Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)=O.[CH3:22][C:23](=O)[CH2:24][C:25](=[O:27])[CH3:26]>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:21][S:18]([C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:24]([C:25](=[O:27])[CH3:26])=[C:23]([CH3:22])[N:1]=[C:2]3[S:6][C:5]4[CH2:7][CH2:8][CH2:9][C:4]=4[C:3]=23)=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 50 mg (0.15 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-methanesulfonyl-phenyl)-methanone (described above) in 2 ml acetic acid was added 0.011 ml (0.15 mmol) of pentane-2,4-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 18 mg (30%) 1-[4-(4-methanesulfonylphenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a light brown solid. ES-MS m/e (%): 386 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-88f1bf8ff8a343ad91565285d5a61e0c
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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