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

HRID 10396

Reaction equation

HRID 10396 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

5

Reactant 3

HCID 8471TriethylamineHCID 641544(R)-2-MethylpyrrolidineHCID 21041502Methanesulfonic acid 2-(5-bromo-benzothiazol-2-yl)-ethyl ester

Product 1

HCID 210414985-Bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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)-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)+.

Workup

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 (twice)
  4. dry with materialThe organic layer as dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give crude product, 1.15 g (97.1%)

Sources & evidence

ORD record
ord-3a282d85555e47b2bfce6f9522c00967
Source dataset
uspto-grants-2006_08
Patent number
US07094790B2

Linked notes

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