Pyridine → HCID 67036917, compound

HRID 216042Notes

Reaction equation

HRID 216042 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[NH2:30][C:31]1[CH:32]=[C:33]([S:37]([NH2:40])(=[O:39])=[O:38])[CH:34]=[CH:35][CH:36]=1>ClC(Cl)C.CN(C=O)C.ClCCl>[CH3:17][C:11]1([C:14](=[O:16])[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([S:37](=[O:39])(=[O:38])[NH2:40])[CH:32]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 7377Benzenesulfonamide, 3-amino-HCID 65578Oxalyl chlorideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acid

Product 1

HCID 67036917HCID 67036917, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (60 mg, 0.25 mmol) in dichloroethane (2.0 mL) were added DMF (2 drops) and pyridine (78 mg, 0.99 mmol), followed by oxalyl chloride (31 mg, 0.25 mmol). The mixture was stirred for 40 minutes, and 3-amino-benzenesulfonamide was added. The mixture was heated at 50° C. for 3 hours, and the mixture was cooled, diluted with dichloromethane, washed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl, dried over MgSO4, and concentrated. Silica gel chromatography (2-5% MeOH:CH2Cl2) gave the title compound in 40% yield. MS (ES+) [M+H]+=398.

Workup

  1. temperaturethe mixture was cooled
  2. washwashed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6035889bb3d04fada903cdea369cbbe9
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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