4-(Pyridin-4-yl)benzoic acid → 1-(5-Chlorobenzofuran-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine

HRID 586214Notes

Reaction equation

HRID 586214 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:39][C:40]1[CH:41]=[CH:42][C:43]2[O:47][C:46]([S:48]([N:51]3[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]3)(=[O:50])=[O:49])=[CH:45][C:44]=2[CH:57]=1>CN(C)C=O>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]2[O:47][C:46]([S:48]([N:51]3[CH2:56][CH2:55][N:54]([C:11](=[O:13])[C:10]4[CH:9]=[CH:8][C:7]([C:4]5[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=5)=[CH:15][CH:14]=4)[CH2:53][CH2:52]3)(=[O:49])=[O:50])=[CH:45][C:44]=2[CH:57]=1

Participants

6

Reactant 4

HCID 15208114-(Pyridin-4-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 223297411-(5-Chlorobenzofuran-2-sulfonyl)piperazine

Product 1

HCID 223297151-(5-Chlorobenzofuran-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazineYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of 4-(4-pyridyl)benzoic acid (133 mg, 0.67 mmol) in dimethylformamide (5 ml) was treated sequentially with 1-hydroxybenzotriazole hydrate (108 mg, 0.8 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (153 mg, 0.8 mmol) and 1-(5-chlorobenzofuran-2-ylsulphonyl) piperazine (201 mg, 0.67 mmol). After stirring overnight the solvent was removed in vacuo and the residue chromatographed (Merck Art 9385 silica, eluting with dichloromethane containing 2% v/v of methanol) to yield 1-(5-chlorobenzofuran-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine as a colourless solid (40 mg), 1H NMR (CDCl3) δ=3.2-3.4 ppm (broad s, 4H), δ=3.6-4.0 ppm (broad s, 4H), δ=7.35 ppm (s, 1H), δ=7.5 ppm (m, 6H), δ=7.7 ppm (m, 3H), δ=8.7 ppm (d, 2H), MS (M+H)+ 482/484.

Workup

  1. customwas removed in vacuo
  2. customthe residue chromatographed (Merck Art 9385 silica
  3. washeluting with dichloromethane containing 2% v/v of methanol)

Sources & evidence

ORD record
ord-acb974efb1734287a65e3205356c3b5e
Source dataset
uspto-grants-2005_08
Patent number
US06936610B2

Reaction notes

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