Triethylamine → HCID 117840780, compound

HRID 714921Notes

Reaction equation

HRID 714921 reaction equation
[CH:1]1([C:4]2([CH2:23]O)[CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)[N:10]=3)[C:5]2=[O:22])[CH2:3][CH2:2]1.CS(Cl)(=O)=O.[CH2:30]([N:32](CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:1]1([C:4]2([CH2:23][C:30]#[N:32])[CH2:8][CH2:7][N:6]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]4[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=4)[N:10]=3)[C:5]2=[O:22])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 117839963HCID 117839963, compound

Product 1

HCID 117840780HCID 117840780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-cyclopropyl-3-(hydroxymethyl)-1-(2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)pyrrolidin-2-one (45 mg) obtained in Example 393 in tetrahydrofuran (1.0 mL) were added methanesulfonyl chloride (15 μL) and triethylamine (29 μL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a solution of the residue in N,N-dimethylformamide (1.0 mL) were added potassium cyanide (36 mg) and sodium iodide (82 mg) at room temperature, and the mixture was stirred overnight at 120° C. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (17 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionTo a solution of the residue in N,N-dimethylformamide (1.0 mL) were added potassium cyanide (36 mg) and sodium iodide (82 mg) at room temperature
  6. stirringthe mixture was stirred overnight at 120° C
  7. additionTo the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe obtained organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-35a0e6fb489f4fa3aadfd6618eea3ae3
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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