Water → HCID 58452767, compound

HRID 70625Notes

Reaction equation

HRID 70625 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[NH:27][C:26](=[O:28])[C:25]([Cl:29])=[CH:24][CH:23]=2)=[CH:15][C@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)=[CH:10][CH:9]=1.O.[Cl-].[NH4+]>C(#N)C>[Cl:29][C:25]1[C:26](=[O:28])[NH:27][C:22](/[C:14](/[C:11]2[CH:12]=[CH:13][C:8]([CH2:7][N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:9][CH:10]=2)=[CH:15]/[C@H:16]2[CH2:20][CH2:19][C:18](=[O:21])[NH:17]2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 31268PyrrolidineHCID 673960336-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one

Product 1

HCID 58452767HCID 58452767, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Separately, pyrrolidine (0.424 mL) was added to a solution of 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one (E:Z=1:2 mixture) (206 mg) in acetonitrile (8.24 mL) at room temperature, and the mixture was stirred at room temperature for one hour. Water and a saturated ammonium chloride solution were sequentially added to the reaction solutions at room temperature, and the mixtures were combined, followed by extraction with chloroform. The organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by preparative TLC (chloroform:methanol=5:1) to give the title compound as a white solid (70 mg, 30%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by preparative TLC (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-d3e64fa0f513486f8b06c29c4a0222c5
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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