Chlorosuccinimide → HCID 54670618, compound

HRID 408020Notes

Reaction equation

HRID 408020 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[N:11]=[CH:12][C:13]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:26][CH2:25][C@H:24]([NH:27][C:28]4[CH:29]=[N:30][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:32][CH:33]=4)[C:23]3=[O:38])[CH2:18][CH2:17]2)=[N:14][CH:15]=1>CC(O)=O>[Cl:1][C:12]1[C:13]([N:16]2[CH2:17][CH2:18][CH:19]([N:22]3[CH2:26][CH2:25][C@H:24]([NH:27][C:28]4[CH:29]=[N:30][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:32][CH:33]=4)[C:23]3=[O:38])[CH2:20][CH2:21]2)=[N:14][CH:15]=[C:10]([Cl:9])[N:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 54671087HCID 54671087, compound

Product 1

HCID 54670618HCID 54670618, compoundYield 30.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-Chlorosuccinimide (0.013 g, 0.098 mmol) was added to a suspension of (S)-1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.034 g, 0.075 mmol) in AcOH (0.3 mL). The mixture was stirred at ambient temperature for 1 hour and then at 50° C. for 1 hour. Acetic acid was removed with a stream of nitrogen. The residue was vigorously stirred in a mixture of 10% Na2S2O3 (1 mL) and EtOAc (1 mL) for 40 minutes. The mixture was partitioned between EtOAc (30 mL) and saturated NaHCO3 (20 mL). Solids which did not dissolve were collected by filtration of the suspension through a 0.45 μm nylon membrane to provide (S)-1-(1-(3,5-dichloropyrazin-2-yl)piperidin-4-yl)-3-(6-(methylsulfonyl)pyridin-3-ylamino)pyrrolidin-2-one (0.011 g, 0.023 mmol, 30%). Mass spectrum (apci) m/z=485.0 (M+H) 487.0. Optical purity of the product was not determined.

Workup

  1. waitat 50° C. for 1 hour
  2. customAcetic acid was removed with a stream of nitrogen
  3. stirringThe residue was vigorously stirred in a mixture of 10% Na2S2O3 (1 mL) and EtOAc (1 mL) for 40 minutes
  4. customThe mixture was partitioned between EtOAc (30 mL) and saturated NaHCO3 (20 mL)
  5. dissolutionSolids which did not dissolve
  6. filtrationwere collected by filtration of the suspension through a 0.45 μm nylon membrane

Sources & evidence

ORD record
ord-43af6879ca8b4c66b4c8fa7f44fa3764
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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