Pyridine → HCID 2303847, compound

HRID 1967490Notes

Reaction equation

HRID 1967490 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[N:27]1([S:33]([C:36]2[CH:37]=[C:38]([CH:42]=[CH:43][CH:44]=2)[C:39](O)=[O:40])(=[O:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(OCC)(=O)C.CN(C=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:39](=[O:40])[C:38]2[CH:42]=[CH:43][CH:44]=[C:36]([S:33]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)(=[O:35])=[O:34])[CH:37]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 97314-FluoroanilineHCID 7678893-(Piperidine-1-sulfonyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2303847HCID 2303847, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoroaniline (41 mg), pyridine (0.06 mL) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (107 mg) were added in that order to a DMF (2.0 mL) solution of 3-(piperidin-1-ylsulfonyl)benzoic acid (100 mg), and stirred at room temperature for 14 hours. Ethyl acetate was added to the reaction liquid, washed twice with 2 M hydrochloric acid, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 5% to 50%, gradient) to give the entitled compound (87 mg, 65%) as a white crystal.

Workup

  1. washwashed twice with 2 M hydrochloric acid
  2. dry with materialdried with sodium sulfate
  3. customThe drying agent was removed through filtration
  4. customthe solvent was evaporated off
  5. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 5% to 50%, gradient)

Sources & evidence

ORD record
ord-bb4d0dd5ce0d43ceb8827d8e88094660
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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