Pyridine → HCID 57920211, compound

HRID 2098377Notes

Reaction equation

HRID 2098377 reaction equation
[CH3:1][C:2]1([C:15](=O)[NH:16]C2C=CC=C(S(=O)(=O)N)C=2)C[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.C(O[C:33]([N:35]1[CH2:40][CH2:39][C:38]([CH3:44])([C:41]([OH:43])=O)[CH2:37][CH2:36]1)=O)(C)(C)C.[N:45]1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[NH2:57][C:58]1[CH:59]=[C:60]([S:64]([NH2:67])(=[O:66])=[O:65])[CH:61]=[CH:62][CH:63]=1>ClC(Cl)C.CN(C=O)C.ClCCl>[CH3:44][C:38]1([C:41]([NH:57][C:58]2[CH:63]=[CH:62][CH:61]=[C:60]([S:64](=[O:65])(=[O:66])[NH2:67])[CH:59]=2)=[O:43])[CH2:37][CH2:36][N:35]([C:33]2[C:3]3[C:2]([CH3:1])=[CH:15][NH:16][C:4]=3[N:5]=[CH:6][N:45]=2)[CH2:40][CH2:39]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 7377Benzenesulfonamide, 3-amino-HCID 65578Oxalyl chlorideHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 67036917Tert-butyl 4-methyl-4-(3-sulfamoylphenylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 57920211HCID 57920211, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Preparation of tert-butyl 4-methyl-4-(3-sulfamoylphenylcarbamoyl)piperidine-1-carboxylate. 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-fc8dc23a6c884fac88fe041942c4a118
Source dataset
uspto-grants-2013_05
Patent number
US08450332B2

Reaction notes

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