Toluene → HCID 86682249, compound

HRID 1428379Notes

Reaction equation

HRID 1428379 reaction equation
[Cl:1][C:2]1[C:6]([N:7]([CH2:20][C:21]#[CH:22])[C:8](=[O:19])[CH2:9][N:10](C)[C:11](=O)OC(C)(C)C)=[CH:5][N:4]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1.FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[C:6]([N:7]([CH2:20][C:21]#[CH:22])[C:8](=[O:19])[CH2:9][NH:10][CH3:11])=[CH:5][N:4]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 86682250HCID 86682250, compound

Product 1

HCID 86682249HCID 86682249, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2-((3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)(prop-2-yn-1-yl)amino)-2-oxoethyl)(methyl)carbamate (0.47 g, 1.16 mmol) in DCM (1.16 ml) was added 2,2,2-trifluoroacetic acid (1.16 ml) and the reaction mixture was stirred at ambient temperature for 1 h. To the mixture was added toluene and then the reaction was concentrated to dryness. The oil was redissolved in DCM and saturated NaHCO3 solution was added. The phases were separated and the aqueous phase was extracted with DCM. The organic layers were combined, the solvent evaporated, and the residue purified using silica gel chromatography (0-15% MeOH/DCM) to afford the title compound as yellow oil (0.258 g, 0.849 mmol, 73%): IR (thin film) 1696 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.98 (d, J=2.6 Hz, 1H), 8.64 (dd, J=4.7, 1.3 Hz, 1H), 8.19 (s, 1H), 8.06 (ddd, J=8.3, 2.6, 1.4 Hz, 1H), 7.47 (dd, J=8.3, 4.7 Hz, 1H), 4.48 (s, 2H), 3.49 (s, 2H), 2.49 (s, 3H), 2.28 (t, J=2.5 Hz, 1H); ESIMS m/z 304 ([M+H]+).

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. dissolutionThe oil was redissolved in DCM
  3. additionsaturated NaHCO3 solution was added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with DCM
  6. customthe solvent evaporated
  7. customthe residue purified

Sources & evidence

ORD record
ord-9b839fc296c64d33bf737c88802bae7f
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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