Triethylamine → N-[3-(3-Fluorophenyl)-1H-5-indazolyl]methanesulfonamide

HRID 1610104Notes

Reaction equation

HRID 1610104 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C(OC(C)(C)C)=O)[N:6]=[C:5]2[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>O1CCCC1.O>[F:24][C:20]1[CH:19]=[C:18]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:3]=3)[NH:7][N:6]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 222606241h-Indazole-1-carboxylic acid,5-amino-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Product 1

HCID 22260964N-[3-(3-Fluorophenyl)-1H-5-indazolyl]methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 mg of tert-butyl 5-amino-3-(3-fluorophenyl)-1H-1-indazolecarboxylate produced in Production Example I-26 in 2 ml tetrahydrofuran were added 30 μl of triethylamine and 15 μl of methanesulfonyl chloride, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was diluted with water and was extracted with ethyl acetate. The organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The resulting crude crystals were recrystallized from ethyl acetate-diethyl ether, to give 26 mg of the title compound as a colorless powder.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was sequentially washed with 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customThe resulting crude crystals were recrystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-7b3669d998634b64bc3f0e7f60c65dbe
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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