Hydrochloric Acid → [1-[4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]acetic acid

HRID 1814026Notes

Reaction equation

HRID 1814026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[N:11]=[C:10](CC#N)[CH:9]=2)=[CH:4][CH:3]=1.Cl.[Li+].[OH-:28].[CH2:29]([OH:31])[CH3:30]>O>[NH2:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:9][C:10]([CH2:30][C:29]([OH:28])=[O:31])=[N:11]2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 3939Lithium HydroxideHCID 108331274-[5-(4-Chloro-phenyl)-3-cyanomethyl-pyrazol-1-yl]-benzenesulfonamide

Product 1

HCID 12052546[1-[4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]acetic acidYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-[5-(4-chlorophenyl)-3-(cyanomethyl)-1H-pyrazol-1-yl]benzenesulfonamide from step 2 (0.340 g, 3.594 mmol) in ethanol (250 mL) at −10° C., HCl gas was added via a fritted gas inlet tube over 6 hours. The reaction mixture was concentrated in vacuo yielding an oil. The oil was dissolved in 50 mL of ethanol and 15 mL of water, treated with LiOH until the pH was 12, and stirred at room temperature overnight. The reaction was concentrated in vacuo, diluted with water, acidified with dil HCl, and extracted with ethyl acetate. The ethyl acetate phase was dried over anhydrous MgSO4, filtered and concentrated yielding [[1-[4-(aminosulfonyl)phenyl]-5-(4-chlorophenyl)-1H-pyrazol-3-yl]acetic acid as a brown solid (1.072 g, 76%): mp 120-122° C. High resolution mass spectrum Calc'd. for C17H15ClN3O4S (M+H): 392.0472. Found: 392.0467. 1 h NMR (CDCl3 and CD3CO2D) 7.84 (d, J=8.66 Hz 2 H), 7.37 (d, J=8.66 Hz, 2 H), 7.31 (d, J=8.66 Hz, 2 H), 7.15 (d, J=8.66 Hz, 2 H), 6.54 (s, 1H), 3.84 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customyielding an oil
  3. concentrationThe reaction was concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate phase was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-96f83770382b4dfdb18b503237c43c3d
Source dataset
uspto-grants-2005_04
Patent number
US06875785B2

Reaction notes

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