Ethanamine, 2,2,2-trifluoro- → 3-(2-{5-[cyclopentyl(methyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-3-phenyl-N-(2,2,2-trifluoroethyl)propanamide

HRID 45265Notes

Reaction equation

HRID 45265 reaction equation
[CH:1]1([N:6]([CH3:33])[S:7]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:20](=[O:21])[C:19]([CH:22]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][C:24]([O-:26])=O)=[CH:18][NH:17]3)=[N:14][CH:15]=2)(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[F:43][C:44]([F:48])([F:47])[CH2:45][NH2:46].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH:1]1([N:6]([CH3:33])[S:7]([C:10]2[CH:11]=[CH:12][C:13]([N:16]3[C:20](=[O:21])[C:19]([CH:22]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:23][C:24]([NH:46][CH2:45][C:44]([F:48])([F:47])[F:43])=[O:26])=[CH:18][NH:17]3)=[N:14][CH:15]=2)(=[O:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86659758HCID 86659758, compound

Product 1

HCID 674555723-(2-{5-[cyclopentyl(methyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-3-phenyl-N-(2,2,2-trifluoroethyl)propanamideYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 200 mg (0.43 mmol) of 3-(2-{5-[cyclopentyl(methyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-3-phenylpropanoate, 0.3 mL (1.7 mmol) of DIEA and 30 μL (0.43 mmol) of 2,2,2-trifluoroethylamine in 1 mL of DCM are added, at 0° C., 207 mg (0.64 mmol) of TBTU. The medium is stirred for 12 hours at room temperature. A further 0.3 mL of 2,2,2-trifluoroethylamine is then added and the medium is heated at 40° C. for 6 hours. The medium is taken up in 20 mL of DCM, washed successively with water (2×10 mL) and brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure, and then purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 32 mg of 3-(2-{5-[cyclopentyl(methyl)sulfamoyl]pyridin-2-yl}-3-oxo-2,3-dihydro-1H-pyrazol-4-yl)-3-phenyl-N-(2,2,2-trifluoroethyl)propanamide are thus obtained in the form of a powder.

Workup

  1. temperaturethe medium is heated at 40° C. for 6 hours
  2. washwashed successively with water (2×10 mL) and brine (20 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 cyclohexane/EtOAc gradient of 0 to 10% EtOAc

Sources & evidence

ORD record
ord-d0da3ef9e6b9428e943310bfba4da527
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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