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

HRID 10396

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)-methyl pyrrolidine (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
washwashed 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-3a282d85555e47b2bfce6f9522c00967
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07094790B2

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