Triethylamine → HCID 70664923, compound

HRID 1854530Notes

Reaction equation

HRID 1854530 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1)=[O:5])C.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].[OH-].[Na+]>C1COCC1>[CH3:25][S:26]([NH:11][C:9]1[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=[C:6]([C:4]([OH:3])=[O:5])[CH:10]=1)(=[O:28])=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 23630921Ethyl 5-amino-1-phenyl-1H-pyrazole-3-carboxylate

Product 1

HCID 70664923HCID 70664923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (2.0 mmol) of 5-Amino-1-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester are dissolved in 10 ml of THF, 0.56 ml (4.0 mmol) of triethylamine and 230 mg (2.0 mmol) of methanesulfonyl chloride are added. The mixture is stirred overnight at RT, the solvent is removed in vacuo and the crude product is subjected to an aqueous work-up and extracted with dichloromethane. The isolated product is dissolved in 10 ml of DMF, 8 mmol 12.5 mmol of 1M NaOH solution are added and the mixture is stirred overnight at RT. The solvent is removed in vacuo and the crude product subjected to HPLC chromatography. Yield after two steps: 170 mg, 30%

Workup

  1. customthe solvent is removed in vacuo
  2. extractionextracted with dichloromethane
  3. dissolutionThe isolated product is dissolved in 10 ml of DMF
  4. stirringthe mixture is stirred overnight at RT
  5. customThe solvent is removed in vacuo
  6. customYield after two steps

Sources & evidence

ORD record
ord-e07c8a1fd36e4e84a14e6f5366ac21e9
Source dataset
uspto-grants-2015_02
Patent number
US08962671B2

Reaction notes

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