Triethylamine → HCID 118500702, compound

HRID 712765Notes

Reaction equation

HRID 712765 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH2:11])[CH3:10])[CH:6]=[N:7][CH:8]=1.C(N(CC)CC)C.[CH2:19]([S:21](Cl)(=[O:23])=[O:22])[CH3:20]>C(Cl)Cl>[Br:2][C:3]1[CH:4]=[C:5]([C@H:9]([NH:11][S:21]([CH2:19][CH3:20])(=[O:23])=[O:22])[CH3:10])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 117667434HCID 117667434, compound

Product 1

HCID 118500702HCID 118500702, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 100-mL flask are added (1R)-1-(5-bromo(3-pyridyl))ethylamine HCl salt (0.5 g, 2.105 mmol), DCM (5 mL), and triethylamine (1.2 mL, 8.52 mmol). The mixture is cooled to 0° C. Ethanesulfonyl chloride (0.24 mL, 2.526 mmol, dissolved in 3 mL of DCM) is added dropwise. The mixture is stirred at 0° C. for 15 min. The ice/water bath is removed and the mixture is stirred at room temperature for 25 min. The mixture is diluted with EtOAc (50 mL), washed with water (3×5 mL), and brine, dried over sodium sulfate, filtered, and concentrated. The resulting crude product is purified by normal phase chromatography using 0-5% MeOH in DCM as the gradient to afford ethanesulfonic acid [(R)-1-(5-bromo-pyridin-3-yl)-ethyl]-amide (482.5 mg, 78% yield).

Workup

  1. customThe ice/water bath is removed
  2. stirringthe mixture is stirred at room temperature for 25 min
  3. additionThe mixture is diluted with EtOAc (50 mL)
  4. washwashed with water (3×5 mL), and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product is purified by normal phase chromatography

Sources & evidence

ORD record
ord-82c6da01f6314d5db610d37652e4e5ac
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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