Acetylacetone → HCID 11500348, compound

HRID 133514Notes

Reaction equation

HRID 133514 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[O:13][CH:14]=[CH:15][CH:16]=1)=O.[CH3:17][C:18](=O)[CH2:19][C:20](=[O:22])[CH3:21]>C(O)(=O)C.S(=O)(=O)(O)O>[O:13]1[CH:14]=[CH:15][CH:16]=[C:12]1[C:10]1[C:19]([C:20](=[O:22])[CH3:21])=[C:18]([CH3:17])[N:1]=[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][C:4]=3[C:3]=12

Participants

5

Reactant 2

HCID 31261AcetylacetoneHCID 9813406HCID 9813406, compound

Product 1

HCID 11500348HCID 11500348, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 50 mg (0.21 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-furan-2-yl-methanone in 2 ml acetic acid was added 0.016 ml (0.21 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 20 mg (31%) 1-(4-furan-2-yl-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a yellow solid. ES-MS m/e (%): 298 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c9dd164a322641138d971b20353d1708
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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