Trifluoroacetic acid → HCID 86682245, compound

HRID 1428375Notes

Reaction equation

HRID 1428375 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:15][C:16]#[CH:17])C(=O)OC(C)(C)C)=[CH:5][N:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:6]([NH:7][CH2:15][C:16]#[CH:17])=[CH:5][N:4]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86682246HCID 86682246, compound

Product 1

HCID 86682245HCID 86682245, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(prop-2-yn-1-yl)carbamate (2.2 g, 6.61 mmol) in dichloromethane (DCM; 8.3 ml) was added 2,2,2-trifluoroacetic acid (12.06 g, 106 mmol) and the reaction mixture was stirred at ambient temperature for 1 h. The reaction was quenched by the addition of saturated sodium bicarbonate (NaHCO3). The organic layer was extracted with DCM (2×20 mL). The organic layers were combined and dried over sodium sulfate (Na2SO4), filtered and concentrated to afford the title compound as a beige solid (1.5 g, 6.12 mmol, 93%): 1H NMR (400 MHz, CDCl3) δ 8.89 (d, J=2.3 Hz, 1H), 8.50 (dd, J=4.7, 1.4 Hz, 1H), 8.01-7.93 (m, 1H), 7.54 (s, 1H), 7.37 (ddd, J=8.3, 4.8, 0.7 Hz, 1H), 3.90 (s, 2H), 3.38 (s, 1H), 2.44-2.09 (m, 1H); ESIMS m/z 233 ([M+H]+).

Workup

  1. customThe reaction was quenched by the addition of saturated sodium bicarbonate (NaHCO3)
  2. extractionThe organic layer was extracted with DCM (2×20 mL)
  3. dry with materialdried over sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-24f42b62b4f447e9b1f0cb789bb32c01
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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