Ethyl Acetate → HCID 178420810, compound

HRID 1846817Notes

Reaction equation

HRID 1846817 reaction equation
[H-].[Na+].[NH:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[C@H:12]1[CH2:15][C@H:14]([OH:16])[CH2:13]1.F[C:18]1[C:23]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:22][CH:21]=[CH:20][N:19]=1.C(OCC)(=O)C>CN(C=O)C>[O:27]1[CH2:28][CH2:29][CH:24]([C:23]2[C:18]([O:16][C@H:14]3[CH2:13][C@H:12]([C:4]4[NH:5][C:6]5[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=5[N:3]=4)[CH2:15]3)=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridineHCID 178521625HCID 178521625, compound

Product 1

HCID 178420810HCID 178420810, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion, 0.049 g, 1.2 mmol) was added to a solution of trans-3-(1H-benzo[d]imidazol-2-yl)cyclobutanol (0.11 g, 0.58 mmol) in DMF (1.5 mL) under argon and the mixture was stirred for 45 min at RT. 2-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine (0.11 g, 0.58 mmol) was added and the mixture was stirred for 16 h at 110° C. Ethyl acetate was added and the mixture was washed with water (2×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to give 2-(trans-3-(3-(Tetrahydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclobutyl)-1H-benzo[d]imidazole (37 mg, 0.11 mmol, 18% yield) as a white solid. [M+1]: 350.3. IC50 (uM) 0.01041.

Workup

  1. stirringthe mixture was stirred for 16 h at 110° C
  2. washthe mixture was washed with water (2×), saturated aqueous sodium chloride (1×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74d5954fdc8449e1b67b7e236e245a18
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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