Trifluoroacetic acid → HCID 178433741, compound

HRID 2402026Notes

Reaction equation

HRID 2402026 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:25]3[C:26]([CH3:34])=[N:27][N:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=34)[S:10][C:11]=2[C:12]2[N:16]=[CH:15][N:14](COCC[Si](C)(C)C)[N:13]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:25]3[C:26]([CH3:34])=[N:27][N:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=34)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][N:13]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667494813-[4-(4-Chlorobenzyl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-2-methylpyrazolo[1,5-a]pyridine

Product 1

HCID 178433741HCID 178433741, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-(4-chlorobenzyl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-thiazol-2-yl]-2-methylpyrazolo[1,5-a]pyridine (0.182 g, 0.339 mmol) in dichloromethane (3.3 mL) at room temperature was added trifluoroacetic acid (5.1 mL, 66 mmol). The mixture was then stirred at room temperature for 3 hours. The solvent was evaporated and the excess trifluoroacetic acid was removed by azeotroping with toluene. The crude product was purified by column chromatography (SiO2, elution with hexane to 100% ethyl acetate) to yield the title compound (0.0884 g, 64%). LCMS: (FA) ES+, 407. 1H NMR (400 MHz, d6-DMSO) δ: 8.76-8.70 (m, 2H), 8.28-8.22 (m, 1H), 7.53-7.46 (m, 1H), 7.45-7.40 (m, 2H), 7.37-7.31 (m, 2H), 7.07-7.01 (m, 1H), 5.55-5.50 (m, 1H), 4.64 (s, 2H), 2.65 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe excess trifluoroacetic acid was removed
  3. customby azeotroping with toluene
  4. customThe crude product was purified by column chromatography (SiO2, elution with hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-2f98c67edfed44c89981eb5264788d12
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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