1-Cyclopropyl-butane-1,3-dione → cyclopropyl-(2-methyl-4-phenyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-methanone

HRID 133527Notes

Reaction equation

HRID 133527 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][CH:15]=[CH:14][CH:13]=1)=O.[CH:18]1([C:21](=[O:26])[CH2:22][C:23](=O)[CH3:24])[CH2:20][CH2:19]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:18]1([C:21]([C:22]2[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:3]3[C:4]4[CH2:9][CH2:8][CH2:7][C:5]=4[S:6][C:2]3=[N:1][C:23]=2[CH3:24])=[O:26])[CH2:20][CH2:19]1

Participants

5

Reactant 2

HCID 110188691-Cyclopropyl-butane-1,3-dioneHCID 142418403-benzoyl-4H,5H,6H-cyclopenta[b]thiophen-2-amine

Product 1

HCID 11551717cyclopropyl-(2-methyl-4-phenyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-methanoneYield 33.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 60 mg (0.24 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 3) in 2 ml acetic acid was added 41 mg (0.32 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 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 27 mg (33%) cyclopropyl-(2-methyl-4-phenyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-3-yl)-methanone as a light brown oil. ES-MS m/e (%): 334 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-43d20c40d4484e1397994fb0f40006cf
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

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