2,4-Dichlorobenzoyl chloride → 2,4-dichloro-N-{[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methyl}benzamide

HRID 2100309Notes

Reaction equation

HRID 2100309 reaction equation
[CH2:1]([S:4]([N:7]1[CH2:10][C:9]([CH2:17][NH2:18])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:8]1)(=[O:6])=[O:5])[CH2:2][CH3:3].CCN(C(C)C)C(C)C.[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>C(Cl)Cl>[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31]([NH:18][CH2:17][C:9]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:10][N:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:5])=[O:6])[CH2:8]1)=[O:32]

Participants

5

Reactant 3

HCID 666452,4-Dichlorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 577983191-[1-(Propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine

Product 1

HCID 116979302,4-dichloro-N-{[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methyl}benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methanamine (II-2, 10 mg, 0.04 mmol) in CH2Cl2 (1 mL) was treated with i-Pr2NEt (0.1 mL, 0.58 mmol), 2,4-dichlorobenzoyl chloride (20 μL, 0.14 mmol), and stirred at room temperature. After 3 h, volatiles were removed under a stream of N2 and the residue purified by reverse phase HPLC to afford 2,4-dichloro-N-{[1-(propylsulfonyl)-3-pyridin-2-ylazetidin-3-yl]methyl}benzamide (II-3) as a white amorphous solid.

Workup

  1. customvolatiles were removed under a stream of N2
  2. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-e48a67448bc447669ddca7d8e9ce1951
Source dataset
uspto-grants-2009_08
Patent number
US07572792B2

Reaction notes

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