Ethyl Acetate → HCID 178481824, compound

HRID 570237Notes

Reaction equation

HRID 570237 reaction equation
[C:1]([C:5]1[C:6]([Cl:41])=[C:7]([C:11]2[NH:40][C:14]3[C:15]([O:29][CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[C:1]([C:5]1[C:6]([Cl:41])=[C:7]([C:11]2[NH:40][C:14]3[C:15]([O:29][CH2:30][CH2:31][OH:32])=[N:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:28])([F:27])[F:26])=[CH:18][C:13]=3[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 178481826HCID 178481826, compound

Product 1

HCID 178481824HCID 178481824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridine (390 mg, 0.641 mmol, prepared as described in the previous step) and tetrabutylammonium fluoride hydrate (914 mg, 3.21 mmol) in THF (10 mL) was stirred at 50° C. for 18 h. After cooling to room temperature, the resulting mixture was treated with EtOAc (50 mL) and washed with H2O (2×20 mL), brine (20 mL). The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (40:60-60:40 EtOAc/heptane) to yield 2-[2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy]-ethanol as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.67 (dd, J=7.3, 2.0 Hz, 1H), 7.48-7.56 (m, 2H), 7.39 (td, J=6.7, 1.8 Hz, 2H), 4.64-4.68 (m, 2H), 4.05 (s, 3H), 3.97-4.02 (m, 2H), 1.42-1.49 (m, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C23H23ClF3N5O2: 492.2 (M+H), Measured: 492.4.

Workup

  1. customprepared
  2. temperatureAfter cooling to room temperature
  3. washwashed with H2O (2×20 mL), brine (20 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (40:60-60:40 EtOAc/heptane)

Sources & evidence

ORD record
ord-69c9e005df974ed28e67348405723cf0
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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