Water → 1-((2'-(N-(methoxycarbonyl)sulfamoyl)biphenyl-4-yl)methyl)-5-propyl-1H-pyrazole-3-carboxylic acid

HRID 1803784Notes

Reaction equation

HRID 1803784 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:30])(=[O:29])[NH2:28])=[CH:17][CH:16]=2)[N:7]=1)=[O:5])C.C(Cl)Cl.Cl[C:35]([O:37][CH3:38])=[O:36].CCN(C(C)C)C(C)C.[Li+].[OH-].O>C1COCC1.CCO>[CH3:38][O:37][C:35]([NH:28][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:8]2[C:9]([CH2:11][CH2:12][CH3:13])=[CH:10][C:6]([C:4]([OH:3])=[O:5])=[N:7]2)=[CH:16][CH:17]=1)(=[O:30])=[O:29])=[O:36]

Participants

9

Reactant 6

HCID 962WaterHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 667578145-Propyl-1-(2'-sulfamoylbiphenyl-4-ylmethyl)-1H-pyrazole-3-carboxylic Acid Ethyl Ester

Product 1

HCID 581029031-((2'-(N-(methoxycarbonyl)sulfamoyl)biphenyl-4-yl)methyl)-5-propyl-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Propyl-1-(2′-sulfamoylbiphenyl-4-ylmethyl)-1H-pyrazole-3-carboxylic acid ethyl ester (80 mg, 0.2 mmol) was dissolved in methylene chloride (2.0 mL, 30.6 mmol). Methyl chloroformate (17.4 μL, 224 μmol) was added, along with DIPEA (81.5 μL, 468 μmol). The mixture was stirred at room temperature for 2 hours. 1 M LiOH in water (1.5 mL, 1.50 mmol) and THF:EtOH 2:1 mL were added and the resulting mixture was stirred for 2 hours. The reaction was quenched with 1 N HCl and DCM (4 mL) was added. The organics were extracted and dried under vacuum to yield the title compound.

Workup

  1. stirringthe resulting mixture was stirred for 2 hours
  2. customThe reaction was quenched with 1 N HCl and DCM (4 mL)
  3. additionwas added
  4. extractionThe organics were extracted
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7015697f6c3645e9aa9257f10c6df182
Source dataset
uspto-grants-2013_01
Patent number
US08350027B2

Reaction notes

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