Trifluoroacetic acid → HCID 71582151, compound

HRID 2359129Notes

Reaction equation

HRID 2359129 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([N:17]2[C:21]3[CH:22]=[C:23]([N:26]4[CH2:31][CH2:30][NH:29][C@H:28]([CH3:32])[CH2:27]4)[CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH3:16])=[C:11]([C:33]([F:36])([F:35])[F:34])[CH:10]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([N:17]2[C:21]3[CH:22]=[C:23]([N:26]4[CH2:31][CH2:30][N:29]([C:3]([C@H:2]5[CH2:11][CH2:12][CH2:15][NH:17]5)=[O:5])[C@H:28]([CH3:32])[CH2:27]4)[CH:24]=[CH:25][C:20]=3[N:19]=[CH:18]2)[CH3:16])=[C:11]([C:33]([F:36])([F:34])[F:35])[CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86688440HCID 86688440, compound

Product 1

HCID 71582151HCID 71582151, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of the crude 1-((R)-1-(4-chloro-2-(trifluoromethyl)phenyl)ethyl)-6-((R)-3-methylpiperazin-1-yl)-1H-benzo[d]imidazole (0.060 g, 0.1 mmol) in dichloromethane (1.5 mL) and the resulting solution was stirred at room temperature for 1 h. Excess solvent was removed in vacuo, and the residue was diluted with dichloromethane (10 mL). The organic layer was neutralized with saturated aqueous sodium bicarbonate, and the aqueous layer was further extracted with dichloromethane (2×15 mL) The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, 0-20% methanol in dichloromethane) to give the title compound as a white solid (0.027 g, 0.052 mmol, 52%). 1H NMR (400 MHz, CDCl3) δ 8.17 (s, 1 H), 7.71 (d, J=2.8 Hz, 1 H), 7.65 (d, J=9.2 Hz, 1 H), 7.37 (d, J=8.8 Hz, 1 H), 6.95-6.90 (m, 2 H), 6.49 (d, J=2.0 Hz, 1 H), 5.84 (q, J=6.8 Hz, 1 H), 4.78-4.84 (m, 1 H), 4.53-4.50 (m, 1 H), 4.25-4.20 (m, 1 H), 3.99-3.84 (m, 1 H), 3.88-3.82 (m, 1 H), 3.71-3.68 (m, 1 H), 3.54-3.51 (m, 1 H), 3.35-3.11 (m, 3 H), 2.87-2.75 (m, 2 H), 2.64-2.58 (m, 2 H), 1.99 (d, J=7.2 Hz, 3 H), 1.44-1.31 (m, 3 H); MS: (ES) m/z calculated for C26H30ClFN5O [M+H]+ 520.2, found 520.4.

Workup

  1. customExcess solvent was removed in vacuo
  2. additionthe residue was diluted with dichloromethane (10 mL)
  3. extractionthe aqueous layer was further extracted with dichloromethane (2×15 mL) The combined organic layers
  4. dry with materialwere dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (SiO2, 0-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-532d399aa8fc47a696cd3212b61c38bb
Source dataset
uspto-grants-2014_04
Patent number
US08685959B2

Reaction notes

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