Triethylamine → Ethyl 7-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-3-ethyl-1H-indole-5-carboxylate

HRID 852658

Reaktionsgleichung

Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][C:10]1[CH:11]=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[C:14]2[C:18]=1[NH:17][CH:16]=[C:15]2[CH2:19][CH3:20])(=[O:8])=[O:7].CCN(CC)CC>CCO>[O:7]=[S:6]1(=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][N:9]1[C:10]1[CH:11]=[C:12]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:13]=[C:14]2[C:18]=1[NH:17][CH:16]=[C:15]2[CH2:19][CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a solution of ethyl 7-{[(4-chlorobutyl)sulfonyl]amino}-3-ethyl-1H-indole-5-carboxylate (D242) (230 mg, 0.59 mmol, 1 equiv) in EtOH (10 ml) was added NEt3 (249 μl, 1.78 mmol, 3 equiv) and the resulting solution was stirred at 70° C. for 3 h. NEt3 (1 ml, excess) was added and the solution was stirred at the same temperature for 15 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 3/7) gave ethyl 7-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-3-ethyl-1H-indole-5-carboxylate (B148) (150 mg, 72%) as a colorless oil. [M−H]−=349.3, RT=3.10 min.

Aufarbeitung

stirringthe solution was stirred at the same temperature for 15 h
temperaturethen cooled to room temperature
concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in AcOEt
washthe organic phase was washed with a 2N aqueous HCl solution
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 3/7)

Quellen und Nachweise

ORD-Eintrag: ord-b7c60fc36d704f8c98e446e2710f7aa7
Quelldatensatz: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07253198B2

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