Triethylamine → 5-Bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole

HRID 424938

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][CH2:11]OS(C)(=O)=O)=[N:7][C:6]=2[CH:17]=1.[CH3:18][C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1.CCN(CC)CC>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][CH2:11][N:20]3[CH2:21][CH2:22][CH2:23][C@H:19]3[CH3:18])=[N:7][C:6]=2[CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

The methanesulfonic acid 2-(5-bromo-benzothiazol-2-yl)-ethyl ester from Example 1B, and 2 equivalents (7.3 mmol) of 2-(R)-methylpyrrolidine (at a concentration of 10 mg/mL solution in acetonitrile), was combined with excess Et3N (0.99 g, 9.8 mmol), and the resulting mixture was heated to 60° C. for 2 hr. The solvent was removed under vacuum, and the residue dissolved in CH2Cl2. and washed with saturated NaHCO3 (twice). The organic layer as dried over MgSO4 and concentrated in vacuo to give crude product, 1.15 g (97.1%). 1H NMR (400 MHz, CDCl3) δ ppm 1.06 (d, J=6.04 Hz, 3 H) 1.78-1.6 (m, 3 H) 1.88 (m, 1H) 2.20 (m, 1 H) 2.38 (m, 1H) 2.55 (m, 1H) 3.23 (m, 4 H) 7.37 (dd, J=8.44, 1.85 Hz, 1 H) 7.61 (d, J=8.51 Hz, 1 H) 8.02 (d, J=1.92 Hz, 1 H). MS m/z 125,127 (M+H)+, (M+3H)+.

Aufarbeitung

customThe solvent was removed under vacuum
dissolutionthe residue dissolved in CH2Cl2
washand washed with saturated NaHCO3 (twice)
dry with materialThe organic layer as dried over MgSO4
concentrationconcentrated in vacuo
customto give crude product, 1.15 g (97.1%)

Quellen und Nachweise

ORD-Eintrag: ord-040ac4afe6524f449eb303df14d9c18d
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08106088B2

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