1-Cyclopropyl-butane-1,3-dione → HCID 11661922, compound

HRID 133538Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:4]=2[C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)=O.[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>[CH:22]1([C:25]([C:26]2[C:27]([CH3:28])=[N:1][C:2]3[S:6][C:5]4[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:4]=4[C:3]=3[C:12]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[O:30])[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 36 mg (0.11 mmol) (2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-3-yl)-(3,4-dichloro-phenyl)-methanone in 2 ml acetic acid was added 18 mg (0.11 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 10 mg (19%) cyclopropyl-[4-(3,4-dichlorophenyl)-2-methyl-6,7,8,9-tetrahydro-5H-10-thia-1-aza-benzo[a]azulen-3-yl)-methanone as a light yellow oil. ES-MS m/e (%): 430 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-365e31afe47a4f52975954ebc136e1d2
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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