Triethylsilane → HCID 68182982, compound

HRID 1615513Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[S:16][C:12]=3[S:11](=[O:24])(=[O:23])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[CH:14]=[C:15]([C:17]4[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=4)[S:16][C:12]=3[S:11](=[O:24])(=[O:23])[NH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(4-chlorophenyl)-6-pyridin-4-yl-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (25 mg, 0.064 mmol) was suspended in 1,2-Dichloroethane (1.0 mL) and triethylsilane (0.1016 mL, 0.6363 mmol) and Trifluoromethanesulfonic acid (0.02815 mL, 0.3182 mmol) were added to a pressure tube and the resulting yellowish solution was heated at 90° C. overnight. At that time, LCMS indicated mainly the product of elimination. Mixture was cooled to room temperature, solid NaHCO3 (20 mg) was added, mixture was filtered and the filtrate was absorbed on silica gel (1 g). The material was purified by ISCO using DCM to 10% MeOH in DCM over 10 minutes to afford the title compound (10 mg, 42%). LCMS: (FA) ES+ 375, 377. 1H NMR (400 MHz, d6-DMSO) δ: 8.63 (dd, J=4.60, 1.62 Hz, 2H), 7.79 (dd, J=4.58, 1.63 Hz, 2H), 7.64 (s, 1H), 7.51 (s, 4H), 7.06 (s, 1H).

Workup

temperatureMixture was cooled to room temperature
filtrationmixture was filtered
customthe filtrate was absorbed on silica gel (1 g)
customThe material was purified by ISCO
customover 10 minutes

Sources & evidence

ORD record: ord-625e5119b05442acb7c521da4a6f43c5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765746B2

Reaction notes

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