2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-malonic acid dibenzyl ester → [5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acid

HRID 858068Notes

Reaction equation

HRID 858068 reaction equation
C([O:8][C:9](=[O:39])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([C:31]2[C:32]([CH3:38])=[N:33][N:34]([CH3:37])[C:35]=2[Cl:36])(=[O:30])=[O:29])=[CH:23][N:22]=1)C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[Cl:36][C:35]1[N:34]([CH3:37])[N:33]=[C:32]([CH3:38])[C:31]=1[S:28]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:10][C:9]([OH:39])=[O:8])=[N:22][CH:23]=1)(=[O:30])=[O:29]

Participants

4

Reactant 1

HCID 691152402-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-malonic acid dibenzyl ester

Product 1

HCID 58762844[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acidYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-malonic acid dibenzyl ester in ethyl acetate was treated with 10% palladium on carbon. The mixture was hydrogenolyzed at 25° C. under hydrogen at 1 atmosphere until no starting material remained. At this time, the reaction mixture was filtered through celite. The filtrate was concentrated in vacuo to afford [5-(5-chloro-1,3-dimethyl-1H-pyrazole-4-sulfonylamino)-pyridin-2-yl]-acetic acid (94%) as a colorless solid; LRMS for C12H13ClN4O4S (M+H)+ at m/z=345/347.

Workup

  1. customwas hydrogenolyzed at 25° C. under hydrogen at 1 atmosphere until no starting material
  2. filtrationAt this time, the reaction mixture was filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fbe4adcc2e6b4e8db40ad44d6900ea57
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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