1-Cyclopropyl-butane-1,3-dione → Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone

HRID 133539Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][C:11]2[C:14]([C:18](=O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:15]([NH2:17])[S:16][C:10]=2[CH2:9]1)=O)(C)(C)C.[CH:26]1([C:29](=[O:34])[CH2:30][C:31](=O)[CH3:32])[CH2:28][CH2:27]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:26]1([C:29]([C:30]2[C:31]([CH3:32])=[N:17][C:15]3[S:16][C:10]4[CH2:9][NH:8][CH2:13][CH2:12][C:11]=4[C:14]=3[C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:34])[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 1.0 g (2.79 mmol) 2-amino-3-benzoyl-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid tert-butyl ester (the preparation of which is described in example 23) in 15 ml acetic acid was added 0.70 g (5.55 mmol) of 1-cyclopropyl-butane-1,3-dione and three drops of sulfuric acid. The mixture was then stirred at 100° C. for 30 minutes and then concentrated in vacuo. Flash chromatography (dichloromethane/methanol 95:5) afforded 0.47 g (48%) cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone as a brown oil. ES-MS m/e (%): 349 (M+H+, 100).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c77921f3aacf460cbc0a99c4457a27e2
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390903B2

Reaction notes

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