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

HRID 1627783Notes

Reaction equation

[NH2:1][C:2]1[S:17][C:5]2[CH2:6][N:7]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:8][CH2:9][C:4]=2[C:3]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=O.O=[C:28]([CH3:39])[CH2:29][CH:30]([CH2:36][CH2:37][CH3:38])[C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl[Si](C)(C)C>CN(C=O)C>[CH2:10]([N:7]1[CH2:6][C:5]2[S:17][C:2]3[N:1]=[C:28]([CH3:39])[C:29]([CH:30]([CH2:36][CH2:37][CH3:38])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=4)[C:3]=3[C:4]=2[CH2:9][CH2:8]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-amino-6-benzyl-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 (4 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. After cooling, the volatiles were removed under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of methanol (1-20%) in dichloromethane furnished the title compound as a dark oil.

Workup

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

Sources & evidence

ORD record: ord-044df180a654402e9455f758312e4951
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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