Hydrochloric Acid → HCID 178424412, compound

HRID 1015654Notes

Reaction equation

HRID 1015654 reaction equation
C([O:5][C:6]([C:8]1[S:9][C:10]([C:24]2[CH:28]=[CH:27][N:26](S(=O)(=O)N(C)C)[N:25]=2)=[CH:11][C:12]=1[NH:13][S:14]([C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1)(=[O:16])=[O:15])=[O:7])(C)(C)C.Cl>O1CCOCC1.CO.O>[NH:26]1[CH:27]=[CH:28][C:24]([C:10]2[S:9][C:8]([C:6]([OH:7])=[O:5])=[C:12]([NH:13][S:14]([C:17]3[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[CH:11]=2)=[N:25]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 20775777HCID 20775777, compound

Product 1

HCID 178424412HCID 178424412, compoundYield 65.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A reaction mixture of 5-(1-Dimethylsulfamoyl-1H-pyrazol-3-yl)-3-(toluene-2-sulfonylamino)-thiophene-2-carboxylic acid tert-butyl ester (10 mg, 0.019 mmol) and 4N HCl (0.3 mL) solution in dioxane in MeOH (0.3 mL) was stirred at room temperature 26 h. Reaction mixture was then diluted with water and extracted with EtOAc, concentrated and purified on preparative TLC using MeOH/CH2Cl2/AcOH (5:95:1) furnished the 5-(1H-Pyrazol-3-yl)-3-(toluene-2-sulfonylamino)-thiophene-2-carboxylic acid (4.5 mg, 65.2% yield). 1H NMR (CD3OD, 400 MHz) 7.99 (d, J=7.9 Hz, 1H), 7.81 (s, 1H), 7.43 (t, J=7.5, 1.3 Hz, 1H), 7.42-7.26 (m, 2H), 7.19 (s, 1H), 2.69 (s, 3H).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. concentrationconcentrated
  4. custompurified on preparative TLC

Sources & evidence

ORD record
ord-5313f2c6902a4748bd2df340ddc993c5
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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