Hydrochloric Acid → HCID 68828117, compound

HRID 2100304Notes

Reaction equation

HRID 2100304 reaction equation
[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C@H:7]([C:9]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)[CH3:8])=[O:5].Cl>O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C@H:7]([C:9]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH2:12][NH:11][CH2:10]1)[CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57798315HCID 57798315, compound

Product 1

HCID 68828117HCID 68828117, compoundYield 227.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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. concentrationbefore being concentrated under reduced pressure

Sources & evidence

ORD record
ord-f9275032a8c748e9b67b24c773e078d8
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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