Trifluoroacetic acid → HCID 178489758, compound

HRID 1911337Notes

Reaction equation

HRID 1911337 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:37]=[C:38]([O:40][CH3:41])[CH:39]=1)[CH2:13][CH2:14][C:15]1[CH:19]=[C:18]([NH:20][C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][CH:23]=2)[N:17](C(OC(C)(C)C)=O)[N:16]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:13][CH2:14][C:15]2[CH:19]=[C:18]([NH:20][C:21](=[O:29])[C:22]3[CH:23]=[CH:24][C:25]([I:28])=[CH:26][CH:27]=3)[NH:17][N:16]=2)[CH:37]=[C:38]([O:40][CH3:41])[CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66589816HCID 66589816, compound

Product 1

HCID 178489758HCID 178489758, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.85 mL, 50.02 mmol) was added in one portion to tert-butyl 3-(3,5-dimethoxyphenethyl)-5-(4-iodobenzamido)-1H-pyrazole-1-carboxylate (288 mg, 0.5 mmol) in DCM (10 mL) at room temperature. The resulting solution was stirred for 24 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (5 mL). The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 3.5M NH3/Methanol and pure fractions were evaporated to dryness to afford a tan solid. The solid was triturated with DCM to give the title compound (58.0 mg, 24.3%) as a white solid; 1H NMR (399.9 MHz, DMSO-d6) δ 2.88 (4H, s), 3.73 (6H, s), 6.33 (1H, t), 6.42 (2H, d), 6.47 (1H, s), 7.77 (2H, d), 7.87 (2H, d), 10.73 (1H, s), 12.17 (1H, s).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in MeOH (5 mL)
  3. customThe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness
  6. customto afford a tan solid
  7. customThe solid was triturated with DCM

Sources & evidence

ORD record
ord-aa64f73933fb4ace98e74bd3590e5e36
Source dataset
uspto-grants-2013_12
Patent number
US08604022B2

Reaction notes

Loading…