Water → Ethyl [7-acetyl-2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl]pentanoate

HRID 1627935Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)=O)=[C:11]([NH2:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])[CH3:2].O=[C:24]([CH3:35])[CH2:25][CH:26]([CH2:32][CH2:33][CH3:34])[C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl[Si](C)(C)C.O>CN(C=O)C>[C:1]([N:4]1[CH2:5][C:6]2[S:12][C:11]3[N:13]=[C:24]([CH3:35])[C:25]([CH:26]([CH2:32][CH2:33][CH3:34])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=4)[C:10]=3[C:7]=2[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (6-acetyl-2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(p-tolyl)methanone (2 g; 6.36 mmol) and ethyl 4-oxo-2-propylpentanoate (1.3 g; 7 mmol) in dry DMF (25 mL) under nitrogen atmosphere was added chlorotrimethylsilane (3.25 mL; 25.45 mmol). The mixture was stirred in a sealed tube and heated at 100° C. for 48 h. After cooling, water (25 mL) was added and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of methanol (0-20%) in dichloromethane furnished 2.79 g (94%) of the title compound.

Workup

temperatureAfter cooling
extractionthe resulting mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customPurification by flash-chromatography on silica gel using a gradient of methanol (0-20%) in dichloromethane

Sources & evidence

ORD record: ord-a6c78acb4ef84c9c873d7f3e1e0e859d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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