HCID 69709114, compound → HCID 57714111, compound

HRID 1163019Notes

Reaction equation

HRID 1163019 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]([C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21](C(O)=O)[CH2:20][CH2:19]2)=[CH:5][N:4]=1)#[N:2]>O1CCOCC1.Cl>[CH3:12][C:11]([CH3:14])([CH3:13])[CH2:10][NH:9][C:7]1[C:6]([C:15]#[C:16][CH2:17][N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:5][N:4]=[C:3]([C:1]#[N:2])[N:8]=1

Participants

4

Reactant 1

HCID 69709114HCID 69709114, compound

Product 1

HCID 57714111HCID 57714111, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-{3-[2-cyano-4-(2,2-dimethyl-propylamino)-pyrimidin-5-yl]-prop-2-ynyl}-piperazine-1-carboxylic acid .tert.-butyl ester (2.9 mmol) in dioxane (5 ml), 4N hydrogenchloride in dioxane (15 ml) is added at 0° C. The reaction mixture is stirred at room temperature for 1 day and then evaporated under reduced pressure. To a solution of residual solid, CH2Cl2 is added at room temperature, pH is adjusted to 9.0 by triethylamine. The mixture is quenched with ammonium chloride and extracted with CH2Cl2. The combined extracts are washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue is purified by silica gel column chromatography to afford title compound in 72% yield. Rf=0.11 (MeOH:CH2Cl2=1:9)

Workup

  1. customevaporated under reduced pressure
  2. additionTo a solution of residual solid, CH2Cl2 is added at room temperature
  3. customThe mixture is quenched with ammonium chloride
  4. extractionextracted with CH2Cl2
  5. washThe combined extracts are washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3dfb94b4481e45339a566bcf39d9391f
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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