4-(Pyridin-4-yl)benzoic acid → HCID 22329715, compound

HRID 353457Notes

Reaction equation

HRID 353457 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:57]=[CH:56][C:43]2[O:44][C:45]([S:47]([N:50]3[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]3)(=[O:49])=[O:48])=[CH:46][C:42]=2[CH:41]=1>CN(C)C=O>[Cl:39][C:40]1[CH:57]=[CH:56][C:43]2[O:44][C:45]([S:47]([N:50]3[CH2:51][CH2:52][N:53]([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)[CH2:54][CH2:55]3)(=[O:48])=[O:49])=[CH:46][C:42]=2[CH:41]=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 22329715HCID 22329715, compoundYield 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 (HOBT, 108 mg, 0.8 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC, 153 mg, 0.8 mmol) and 1-(5-chlorobenzo[b]furan-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-chlorobenzo[b]furan-2-ylsulphonyl)-4-[4-(4-pyridyl)benzoyl]piperazine as a colourless solid (40 mg), 1H NMR (CDCl3) 3.2-3.4 ppm (broad s, 4H), 3.6-4.0 ppm (broad s, 4H), 7.35 ppm (s, 1H), 7.5 ppm (m, 6H), 7.7 ppm (m, 3H), 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-2949bbab02eb4ca98f991bfc91ce66ec
Source dataset
uspto-grants-2004_06
Patent number
US06753331B1

Reaction notes

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