HCID 10118758, compound → HCID 10180311, compound

HRID 2223896Notes

Reaction equation

HRID 2223896 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[NH:31]C(=O)OC(C)(C)C)[CH2:18][CH2:17]2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[N:6][CH:7]=1.Cl.C(OCC)(=O)C>CO>[NH2:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][CH2:23][CH2:22][N:19]1[CH2:20][CH2:21][CH:16]([N:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 10118758HCID 10118758, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 10180311HCID 10180311, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl [2-[3-[4-[N-(5-metylpyridin-2-yl)-2-furancarboxamido]piperidin-1-yl]propyl]phenyl]carbamate (790 mg) in methanol (15 mL) was added a 4N hydrochloric acid/ethyl acetate solution (2.3 mL) at room temperature. The solution was stirred at room temperature for 16 hours. The solution was then concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the residue and the solution was extracted with chloroform. The extract was dried over over anhydrous sodium sulfate, and then, concentrated under reduced pressure to give the title compound (700 mg).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  3. extractionthe solution was extracted with chloroform
  4. dry with materialThe extract was dried over over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da58c37da6c947a6aa7ec0091341a64f
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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