Hydrochloric Acid → HCID 86712961, compound

HRID 1424114Notes

Reaction equation

HRID 1424114 reaction equation
[Si]([O:8][CH2:9][C:10]1([CH3:34])[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[CH:30]=[N:31][O:32][CH:33]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[O:32]1[CH:33]=[C:29]([C:26]2[CH:27]=[CH:28][C:23]([C:20]3([C:17]4[N:13]5[CH2:14][CH2:15][S:16][C:10]([CH2:9][OH:8])([CH3:34])[CH2:11][C:12]5=[N:19][N:18]=4)[CH2:22][CH2:21]3)=[CH:24][CH:25]=2)[CH:30]=[N:31]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86712960HCID 86712960, compound

Product 1

HCID 86712961HCID 86712961, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the compound (127 mg, 0.26 mmol) obtained in Example 74-1) and 4 M hydrochloric acid (1,4-dioxane solution, 2 mL) in methanol (10 mL) was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate (10 mL) was added to the residue, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After concentration under reduced pressure, the residue was purified by silica gel chromatography (ethyl acetate:methanol=20:80) to obtain the title compound (20 mg, 20%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate (10 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by silica gel chromatography (ethyl acetate:methanol=20:80)

Sources & evidence

ORD record
ord-4b145a03633546c28a24408e11068e3e
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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