1-Propanesulfonyl chloride → 1-(Propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile

HRID 2100307Notes

Reaction equation

HRID 2100307 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:12]#[N:13])[CH2:11][NH:10][CH2:9]1.CCN(C(C)C)C(C)C.[CH2:23]([S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH3:25]>C(Cl)Cl>[CH2:23]([S:26]([N:10]1[CH2:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)([C:12]#[N:13])[CH2:11]1)(=[O:28])=[O:27])[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 688271533-Pyridin-2-ylazetidine-3-carbonitrile hydrochloride

Product 1

HCID 577983111-(Propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-pyridin-2-ylazetidine-3-carbonitrile hydrochloride (365 mg, 1.9 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with i-Pr2NEt (1.1 mL, 6.3 mmol) and n-PrSO2Cl (0.35 mL, 3.1 mmol) dropwise. After 4 h, the reaction was quenched with the addition of 2 M aqueous NaOH (10 mL) and stirred 72 h before being extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford 1-(propylsulfonyl)-3-pyridin-2-ylazetidine-3-carbonitrile (II-1) as an orange oil. Analytical LCMS: single peak (214 nm), 2.664 min. This material was used in subsequent reactions without further purification.

Workup

  1. customthe reaction was quenched with the addition of 2 M aqueous NaOH (10 mL)
  2. extractionbefore being extracted with CH2Cl2 (3×20 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85be5606e24a4953b3d6be03293ed9a8
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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