1,4-Dioxane hydrochloride → HCID 71465953, compound

HRID 1424139Notes

Reaction equation

HRID 1424139 reaction equation
[Si]([O:8][CH2:9][C@:10]1([CH3:37])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[N:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=5)=[CH:25][C:24]=4[F:36])[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl.O1CCOCC1>CO>[F:36][C:24]1[CH:25]=[C:26]([C:29]2[N:30]=[N:31][C:32]([CH3:35])=[CH:33][CH:34]=2)[CH:27]=[CH:28][C:23]=1[C:20]1([C:17]2[N:13]3[CH2:14][CH2:15][S:16][C@:10]([CH2:9][OH:8])([CH3:37])[CH2:11][C:12]3=[N:19][N:18]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86712983HCID 86712983, compound

Product 1

HCID 71465953HCID 71465953, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (366 mg, 0.68 mmol) obtained in Example 89-2) was dissolved in methanol (4 mL). 4 N hydrochloric acid-dioxane (1.69 mL) was added to the solution, and the mixture was stirred at room temperature for 2 h. The solvent was distilled off under reduced pressure, and the residue was separated into organic and aqueous layers with methylene chloride (150 mL) and saturated aqueous sodium hydrogencarbonate (50 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (methanol:ethyl acetate=0:100 to 20:80) to obtain the title compound (210 mg, 73%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was separated into organic and aqueous layers with methylene chloride (150 mL) and saturated aqueous sodium hydrogencarbonate (50 mL)
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (methanol:ethyl acetate=0:100 to 20:80)

Sources & evidence

ORD record
ord-a323501aa21c420394358542d53028ce
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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