1-Cyclopropyl-butane-1,3-dione → HCID 11516675, compound

HRID 133535Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:13]3[CH2:20][CH2:19][CH2:18][C:14]=3[S:15][C:16]=2[NH2:17])=O)=[CH:6][CH:5]=1.[CH:22]1([C:25](=[O:30])[CH2:26][C:27](=O)[CH3:28])[CH2:24][CH2:23]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:26]([C:25]([CH:22]3[CH2:24][CH2:23]3)=[O:30])=[C:27]([CH3:28])[N:17]=[C:16]3[S:15][C:14]4[CH2:18][CH2:19][CH2:20][C:13]=4[C:12]=23)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 60 mg (0.20 mmol) 4-(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonyl)-benzoic acid methyl ester in 2 ml acetic acid was added 33 mg (0.26 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 22 mg (28%) 4-(3-cyclopropanecarbonyl-2-methyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-b]pyridin-4-yl)-benzoic acid methyl ester as a light brown oil. ES-MS m/e (%): 392 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-63905dde663849bd8c760023b09b61d8
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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