Hydrochloric Acid → HCID 23624284, compound

HRID 2189316Notes

Reaction equation

HRID 2189316 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 (0.178 g, 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 min. The mixture is neutralized with 1 N NaOH aqueous solution and saturated NaHCO3 aqueous solution, extracted with CH2Cl2. The extracts are washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give 160 mg of 2-[4-(4-acetyl-piperazin-1-yl)-phenylamino]-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde as a yellow solid.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09c7bb44eadf49b6a5db7820d9e2f902
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

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