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

HRID 133533Notes

Reaction equation

HRID 133533 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]([O:18][CH3:19])=[CH:14][CH:13]=1)=O.[CH:20]1([C:23](=[O:28])[CH2:24][C:25](=O)[CH3:26])[CH2:22][CH2:21]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:20]1([C:23]([C:24]2[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[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:25]=2[CH3:26])=[O:28])[CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 110188691-Cyclopropyl-butane-1,3-dioneHCID 283374403-(4-methoxybenzoyl)-4H,5H,6H-cyclopenta[b]thiophen-2-amine

Product 1

HCID 11494285cyclopropyl-[4-(4-methoxy-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-methanoneYield 22%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 60 mg (0.22 mmol) (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone (the preparation of which is described in example 10) in 2 ml acetic acid was added 37 mg (0.29 mmol) of 1-cyclopropyl-butane-1,3-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 17 mg (22%) cyclopropyl-[4-(4-methoxy-phenyl)-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-methanone as a light brown solid. ES-MS m/e (%): 364 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e94759b9fec4ecda088f4b17e94df55
Source dataset
uspto-grants-2008_06
Patent number
US07390903B2

Reaction notes

Loading…