Water → HCID 117840808, compound

HRID 714869Notes

Reaction equation

HRID 714869 reaction equation
Cl.Cl.[NH:3]1[CH2:6][CH:5]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:18]=[C:17]([N:19]4[CH2:23][CH2:22][C@:21]([CH2:26][CH3:27])([C:24]#[N:25])[C:20]4=[O:28])[CH:16]=[CH:15][N:14]=3)[CH:9]=[N:8]2)[CH2:4]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>O1CCCC1>[CH2:26]([C@:21]1([C:24]#[N:25])[CH2:22][CH2:23][N:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:10]3[CH:9]=[N:8][N:7]([CH:5]4[CH2:6][N:3]([S:37]([CH3:36])(=[O:39])=[O:38])[CH2:4]4)[CH:11]=3)[N:18]=2)[C:20]1=[O:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 117839929HCID 117839929, compound

Product 1

HCID 117840808HCID 117840808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (3R)-1-(2-((1-(azetidin-3-yl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)-3-ethyl-2-oxopyrrolidine-3-carbonitrile dihydrochloride (83 mg) obtained in Example 185 in tetrahydrofuran (5 mL) were added triethylamine (30 μL) and methanesulfonyl chloride (33 μL) at room temperature, and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added water, 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 (ethyl acetate/hexane), and recrystallized (ethyl acetate/hexane) to give the title compound (16 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. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  6. customrecrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75f5ff732b224b099a4825ff440af504
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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