Hydrochloric Acid → HCID 23624284, compound

HRID 2189285Notes

Reaction equation

HRID 2189285 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:29]([CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32])[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([C:26](=[O:28])[CH3:27])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)C.Cl.[OH-].[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1>[C:26]([N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:10]3[N:11]=[CH:12][C:7]4[CH:6]=[C:5]([CH:4]=[O:3])[N:29]([CH:30]([CH2:31][CH3:32])[CH2:33][CH3:34])[C:8]=4[N:9]=3)=[CH:15][CH:16]=2)[CH2:21][CH2:22]1)(=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 58015866HCID 58015866, compound

Product 1

HCID 23624284HCID 23624284, compoundYield 105.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution 1-(4-{4-[6-Diethoxymethyl-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-phenyl}-piperazin-1-yl)-ethanone (178 mg, 0.35 mmol) in 1,4 dioxane (2.8 mL) is added 0.8 mL of concentrated HCl at ambient temperature. The reaction mixture is stirred at ambient temperature for 30 mins. The mixture is neutralized with 1 N NaOH aqueous solution and saturated NaHCO3 aqueous solution, extracted with EtOAc. The organic layer is washed with brine, dried Na2SO4, and concentrated under reduced pressure to give 160 mg of the title compound as a yellow solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with brine, dried Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7f271ed347d4af4b57a536113da59e4
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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