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

HRID 1157706Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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, 3H) 1.78-1.6 (m, 3H) 1.88 (m, 1H) 2.20 (m, 1H) 2.38 (m, 1H) 2.55 (m, 1H) 3.23 (m, 4H) 7.37 (dd, J=8.44, 1.85 Hz, 1H) 7.61 (d, J=8.51 Hz, 1H) 8.02 (d, J=1.92 Hz, 1H). MS m/z 125, 127 (M+H)+, (M+3H)+.

Workup

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%)

Sources & evidence

ORD record: ord-860c9e1a30254b0cb4f6fbb4a8e9413a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807697B2

Reaction notes

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