1-Propanesulfonyl chloride → HCID 11554296, compound

HRID 2100305Notes

Reaction equation

HRID 2100305 reaction equation
Cl.[Cl:2][C:3]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:4]=1[C:5]([NH:7][C@H:8]([C:10]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:13][NH:12][CH2:11]1)[CH3:9])=[O:6].CCN(C(C)C)C(C)C.[CH2:34]([S:37](Cl)(=[O:39])=[O:38])[CH2:35][CH3:36]>C(Cl)Cl>[Cl:2][C:3]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:4]=1[C:5]([NH:7][C@H:8]([C:10]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:13][N:12]([S:37]([CH2:34][CH2:35][CH3:36])(=[O:39])=[O:38])[CH2:11]1)[CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68828117HCID 68828117, compound

Product 1

HCID 11554296HCID 11554296, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A sample of tert-butyl 3-{(1S)-1-[(2,4-dichlorobenzoyl)amino]ethyl}-3-pyridin-2-ylazetidine-1-carboxylate (I-4, 1.35 g, 3.5 mmol) was treated with HCl (40 mL of a 4.0 M solution in dioxane) and stirred at room temperature for 2 h before being concentrated under reduced pressure to afford 2,4-dichloro-N-[(1S)-1-(3-pyridin-2-ylazetidin-3-yl)ethyl]benzamide hydrochloride (1.54 g, 86%) which was used without further purification. A suspension of 2,4-dichloro-N-[(1S)-1-(3-pyridin-2-ylazetidin-3-yl)ethyl]benzamide hydrochloride (1.54 g, 4.4 mmol) in CH2Cl2 (45 mL) at 0° C. was treated with i-Pr2NEt (3.1 mL, 18 mmol) and n-PrSO2Cl (0.75 mL, 6.6 mmol) dropwise. After 3 h, the reaction was quenched with the addition of 1 M aqueous NaOH (50 mL) and stirred 1 h before being extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried (Na2SO4), concentrated under reduced pressure, and purified by reverse phase HPLC to afford 2,4-Dichloro-N-{(1S)-1-[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]ethyl}benzamide (I-5) as a white amorphous solid.

Workup

  1. customwas used without further purification
  2. customthe reaction was quenched with the addition of 1 M aqueous NaOH (50 mL)
  3. extractionbefore being extracted with CH2Cl2 (3×50 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ffe60bd2cbc94efeafa038f2a6d4228b
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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