Trifluoroacetic acid → (S)-1-(6-(1-cyclopropyl-1H-pyrazol-4-yl)-4-(1H-indazol-3-yl)-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

HRID 1485746Notes

Reaction equation

HRID 1485746 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]([C:26](=[O:28])[CH3:27])[C@@H:21]([CH3:29])[CH2:20][N:19]4[C:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32](C4CCCCO4)[N:31]=3)[CH:13]=[N:12]2)[CH2:10][CH2:9]1>ClCCl>[CH:8]1([N:11]2[CH:15]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]([C:26](=[O:28])[CH3:27])[C@@H:21]([CH3:29])[CH2:20][N:19]4[C:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[NH:32][N:31]=3)[CH:13]=[N:12]2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 1180790791-((2S)-6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-3,4-dihydroquinoxalin-1(2H)-yl)ethanone

Product 1

HCID 118078952(S)-1-(6-(1-cyclopropyl-1H-pyrazol-4-yl)-4-(1H-indazol-3-yl)-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 6.49 mmol) was added to a solution of 1-((2S)-6-(1-cyclopropyl-1H-pyrazol-4-yl)-2-methyl-4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-3,4-dihydroquinoxaline-1(2H)-yl)ethanone (0.048 g, 0.097 mmol) in dichloromethane (2.0 mL) and the mixture stirred at rt for 4 h. The reaction mixture was concentrated and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic phase was separated, dried over anhydrous sodium sulfate, filtered, and concentrated to afford (S)-1-(6-(1-cyclopropyl-1H-pyrazol-4-yl)-4-(1H-indazol-3-yl)-2-methyl-3,4-dihydroquinoxalin-1(2H)-yl)ethanone (0.039 g, 98%) as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.76-1.04 (m, 4 H), 1.09-1.33 (m, 3 H), 2.23 (s, 3 H), 3.54-3.77 (m, 2 H), 3.78-3.99 (m, 1 H), 4.36 (br s, 1 H), 6.67-6.85 (m, 1 H), 6.87-7.14 (m, 2 H), 7.26-7.46 (m, 4 H), 7.53 (d, J=8.50 Hz, 1 H), 7.87 (s, 1 H), 12.70-12.87 (m, 1 H). MS (ESI, pos. ion) m/z 413 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2553d7e65fae407dbc89c55df78761bf
Source dataset
uspto-grants-2016_08
Patent number
US09422281B2

Reaction notes

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