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

HRID 1627784Notes

Reaction equation

[NH2:1][C:2]1[S:11][C:5]2[CH2:6][N:7]([CH3:10])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)=O.O=[C:22]([CH3:33])[CH2:23][CH:24]([CH2:30][CH2:31][CH3:32])[C:25]([O:27][CH2:28][CH3:29])=[O:26].Cl[Si](C)(C)C>CN(C=O)C>[CH3:33][C:22]1[C:23]([CH:24]([CH2:30][CH2:31][CH3:32])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:3]2[C:4]3[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][C:5]=3[S:11][C:2]=2[N:1]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)(p-tolyl)methanone (0.286 g; 1 mmol) and ethyl 4-oxo-2-propylpentanoate (0.204 g; 1.1 mmol) in dry DMF (8 mL) under nitrogen atmosphere was added chlorotrimethylsilane (0.511 mL; 4 mmol) dropwise. The mixture was stirred in a sealed tube and heated at 100° C. for 24 h. An extra volume of chlorotrimethylsilane was added (0.100 mL) and the reaction mixture was stirred at 100° C. for 48 h. The volatiles were removed under reduced pressure and the residue was purified by flash-chromatography on silica gel using a gradient of methanol (1-20%) in dichloromethane to furnish the title compound as a dark oil.

Workup

stirringthe reaction mixture was stirred at 100° C. for 48 h
customThe volatiles were removed under reduced pressure
customthe residue was purified by flash-chromatography on silica gel using a gradient of methanol (1-20%) in dichloromethane

Sources & evidence

ORD record: ord-bf505f9ff0d345fb9eff5b64bd3d54b7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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