1,4-Dioxane hydrochloride → HCID 59834726, compound

HRID 271561Notes

Reaction equation

HRID 271561 reaction equation
Cl.O1CCOCC1.[C:8]([C:10]1[N:11]=[CH:12][C:13]2[CH:18]=[C:17]([CH2:19][N:20]3[CH2:25][CH2:24][N:23](C(O)=O)[CH2:22][CH2:21]3)[N:16]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:14]=2[N:15]=1)#[N:9]>CCOCC>[CH3:31][C:30]([CH3:33])([CH3:32])[CH2:29][N:16]1[C:14]2[N:15]=[C:10]([C:8]#[N:9])[N:11]=[CH:12][C:13]=2[CH:18]=[C:17]1[CH2:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86596997HCID 86596997, compound

Product 1

HCID 59834726HCID 59834726, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4N HCl/dioxane is added to 4-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-piperazine-1-carboxylic acid .tert.-butyl ester at 0° C. and stirred at 25° C. for 90 min. Ether is added to the residue to afford a precipitate, which is collected by filtration. The crude product is dissolved in MeOH and purified by reverse phase HPLC. The fractions (fraction Nos. 23-25) are collected and evaporated. The residue is extracted with ethyl acetate. The organic layer is washed with saturated sodium bicarbonate and brine, and dried over magnesium sulfate and filtrated. The solvent is removed by evaporation and dried in vacuo to afford the title compound. yield 58.1%, Rf=0.30 (CH2Cl2:MeOH=8:2). 1H-NMR (400 MHz, CDCl3) δ 1.01(s, 9H), 2.43(br, 4H), 2.90(br, 4H), 3.76(s, 2H), 4.36(s, 2H), 6.57(s, 1H), 8.89(s, 1H),

Workup

  1. customto afford a precipitate, which
  2. filtrationis collected by filtration
  3. dissolutionThe crude product is dissolved in MeOH
  4. custompurified by reverse phase HPLC
  5. customThe fractions (fraction Nos. 23-25) are collected
  6. customevaporated
  7. extractionThe residue is extracted with ethyl acetate
  8. washThe organic layer is washed with saturated sodium bicarbonate and brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltrated
  11. customThe solvent is removed by evaporation
  12. customdried in vacuo

Sources & evidence

ORD record
ord-1dd1899d76bc426982c4f30405f25363
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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