Water → HCID 18456030, compound

HRID 1272343Notes

Reaction equation

HRID 1272343 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1.[F:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]2[C:22]3[C:23]([CH3:35])=[C:24]([N:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)[C:25]([CH3:28])=[C:26]([CH3:27])[C:21]=3[O:20][C:19]2([CH3:37])[CH3:36])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[ClH:8].[ClH:8].[F:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]2[C:22]3[C:23]([CH3:35])=[C:24]([N:29]4[CH2:30][CH2:31][N:32]([CH2:7][C:6]5[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)[CH2:33][CH2:34]4)[C:25]([CH3:28])=[C:26]([CH3:27])[C:21]=3[O:20][C:19]2([CH3:37])[CH3:36])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 22935586HCID 22935586, compound

Product 1

HCID 18456030HCID 18456030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-methoxybenzyl chloride (0.16 mL, 1.2 mmol) was added to a mixture of 1-(3-(6-fluoropyridine-3-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (369 mg, one mmol) obtained in Example 127 and potassium carbonate (138 mg, 1 mmol) in DMF (5 ml) and the mixture was stirred at room temperature for 3 hours. The resulting mixture was poured into water and extracted with ethyl acetate. The organic extract was washed three times using saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain 365 mg (yield 75%) of free salt of title compound. Thereafter, it was treated with 4N hydrogenchloride in ethyl acetate to obtain the title compound as a hydrochloride salt. mp. 218–221° C. (decomposition) (ethyl acetate-ethanol).

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed three times
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-94302e2269a94d8ca498680b78e338ce
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

Loading…