Hydrogen chloride-ethyl acetate → HCID 58293297, compound

HRID 1912445Notes

Reaction equation

HRID 1912445 reaction equation
C(OC([N:8]1[C:12]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]3[C:19]4[CH:26]=[CH:25][NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[CH2:13]2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.Cl.CO>C(Cl)(Cl)Cl>[NH:8]1[C:12]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]3[C:19]4[CH:26]=[CH:25][NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[CH2:13]2)[CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 21866389Hydrogen chloride-ethyl acetateHCID 21893726Hydrochloride methanolHCID 582933867-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester

Product 1

HCID 58293297HCID 58293297, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,7-diazaspiro[4.5]decane-1-carboxylic acid tert-butyl ester (60 mg) in chloroform (1.0 ml) were added 4M hydrochloric acid-ethyl acetate (1.5 ml) and 2M hydrochloric acid-methanol (0.5 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and then azeotroped with toluene. The residue was neutralized by the addition of 4M aqueous sodium hydroxide solution, and thereto was added saturated aqueous sodium chloride solution. The mixture was extracted with chloroform. The separated organic solvent was concentrated under reduced pressure to give the titled compound (30 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customazeotroped with toluene
  3. additionThe residue was neutralized by the addition of 4M aqueous sodium hydroxide solution
  4. additionwas added saturated aqueous sodium chloride solution
  5. extractionThe mixture was extracted with chloroform
  6. concentrationThe separated organic solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf85616bd4cd4d88a61d5c30ad58fec8
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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