Trifluoroacetic acid → 4-{3-[(6-Chloro-4-o-tolyl-pyridazin-3-yl)-methyl-carbamoyl]-5-trifluoromethyl-benzenesulfonyl}-butyric acid

HRID 403393Notes

Reaction equation

HRID 403393 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH2:9][S:10]([C:13]1[CH:18]=C(C)[CH:16]=[C:15]([C:20](=[O:37])[N:21]([C:23]2[N:24]=[N:25][C:26]([Cl:36])=[CH:27][C:28]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH3:22])[CH:14]=1)(=[O:12])=[O:11])(C)(C)C.C1(OC)C=CC=CC=1.[F:47][C:48]([F:53])([F:52])[C:49](O)=O>ClCCl>[Cl:36][C:26]1[N:25]=[N:24][C:23]([N:21]([CH3:22])[C:20]([C:15]2[CH:14]=[C:13]([S:10]([CH2:9][CH2:8][CH2:7][C:6]([OH:38])=[O:5])(=[O:12])=[O:11])[CH:18]=[C:49]([C:48]([F:53])([F:52])[F:47])[CH:16]=2)=[O:37])=[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH:27]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 866984814-{3-[(6-Chloro-4-o-tolyl-pyridazin-3-yl)-methyl-carbamoyl]-5-methyl-benzenesulfonyl}-butyric acid tert-butyl ester

Product 1

HCID 717662294-{3-[(6-Chloro-4-o-tolyl-pyridazin-3-yl)-methyl-carbamoyl]-5-trifluoromethyl-benzenesulfonyl}-butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{3-[(6-chloro-4-o-tolyl-pyridazin-3-yl)-methyl-carbamoyl]-5-methyl-benzenesulfonyl}-butyric acid tert-butyl ester (0.055 g, 89.9 μmol) in dichloromethane (1.5 mL) were added anisole (10.7 mg, 10.8 μL, 98.8 μmol) and trifluoroacetic acid (512 mg, 346 μL, 4.49 mmol) and the light yellow solution was stirred at room temperature for 3.5 hours. The reaction mixture was evaporated to dryness and the residue treated with toluene and again completely evaporated. The product was purified by preparative HPLC (Gemini NX column) using a gradient of methanol:water (containing 0.1% formic acid) (20:80 to 98:2). Colorless foam (0.037 g; 74%). MS (ESI+): m/z=556.09 ([M+H]+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionthe residue treated with toluene
  3. customagain completely evaporated
  4. customThe product was purified by preparative HPLC (Gemini NX column)

Sources & evidence

ORD record
ord-d0e76d6839fd4653b16588e8e41c372e
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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