1-Cyclopropyl-butane-1,3-dione → HCID 11567954, compound

HRID 133537Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:13]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:14]=3[S:15][C:16]=2[NH2:17])=O)=[CH:6][CH:5]=1.[CH:24]1([C:27](=[O:32])[CH2:28][C:29](=O)[CH3:30])[CH2:26][CH2:25]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:12]3[C:13]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:14]=4[S:15][C:16]=3[N:17]=[C:29]([CH3:30])[C:28]=2[C:27]([CH:24]2[CH2:26][CH2:25]2)=[O:32])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 20 mg (0.06 mmol) 4-(2-Amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonyl)-benzoic acid methyl ester in 1 ml acetic acid was added 10 mg (0.06 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 11 mg (44%) 4-(3-cyclopropanecarbonyl-2-methyl-6,7,8,9-tetrahydro-5H-10-thia-1-aza-benzo[a]azulen-4-yl)-benzoic acid methyl ester as a light yellow solid. ES-MS m/e (%): 420 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-45616fbebd014e97bbc36f7907d1d3b6
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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