Methylamine → 2-(2-{5-[ethyl(phenyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-N-methylacetamide

HRID 45234Notes

Reaction equation

HRID 45234 reaction equation
[CH2:1]([N:3]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:4]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][NH:14]2)=[N:11][CH:12]=1)(=[O:6])=[O:5])[CH3:2].C[CH2:30][N:31](C(C)C)C(C)C.CN.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH2:1]([N:3]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:4]([C:7]1[CH:8]=[CH:9][C:10]([N:13]2[C:17](=[O:18])[C:16]([CH2:19][C:20]([NH:31][CH3:30])=[O:22])=[CH:15][NH:14]2)=[N:11][CH:12]=1)(=[O:6])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68758596(2-{5-[ethyl(phenyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)acetic acid

Product 1

HCID 674539162-(2-{5-[ethyl(phenyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-N-methylacetamideYield 6.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.28 g (0.7 mmol) of (2-{5-[ethyl(phenyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)acetic acid, 0.61 mL (3.48 mmol) of DIEA and 0.8 mL (1.4 mmol) of methylamine (2N solution in THF) in 2 mL of DCM is added at 0° C. 0.33 g (1.04 mmol) of TBTU. After stirring for 3 hours at room temperature, the medium is taken up in 500 mL of DCM, washed successively with 0.1N HCl (2×40 mL), saturated NaHCO3 solution (2×40 mL) and brine (30 mL), dried over Na2SO4 and then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a 95/5 DCM/MeOH mixture. 18 mg of 2-(2-{5-[ethyl(phenyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-N-methylacetamide are obtained in the form of a brown powder.

Workup

  1. additionis added at 0° C
  2. washwashed successively with 0.1N HCl (2×40 mL), saturated NaHCO3 solution (2×40 mL) and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by chromatography on a column of silica gel
  6. washeluting with a 95/5 DCM/MeOH mixture

Sources & evidence

ORD record
ord-0637e60f072a49dabe661f1884dd363d
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

Loading…