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Water → (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one

HRID 407986
Notes
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Reaction equation

HRID 407986 reaction equation
Cl.[Br:2][C:3]1[C:21]([CH3:22])=[CH:20][C:6]([O:7][C@H:8]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:9]2=[O:19])=[C:5]([F:23])[CH:4]=1.C(N(C(C)C)C(C)C)C.Cl[C:34]1[N:39]=[CH:38][C:37]([CH2:40][CH3:41])=[CH:36][N:35]=1.O>CS(C)=O>[Br:2][C:3]1[C:21]([CH3:22])=[CH:20][C:6]([O:7][C@H:8]2[CH2:12][CH2:11][N:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:34]4[N:39]=[CH:38][C:37]([CH2:40][CH3:41])=[CH:36][N:35]=4)[CH2:15][CH2:14]3)[C:9]2=[O:19])=[C:5]([F:23])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 67469732(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride

Product 1

HCID 54671182(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-oneYield 59.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

(S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride (600 mg, 1.47 mmol) was dissolved in DMSO (10 mL) and N-ethyl-N-isopropylpropan-2-amine (641 μl, 3.68 mmol) and 2-chloro-5-ethylpyrimidine (252 mg, 1.77 mmol) were added and the reaction heated to 110° C. overnight. The reaction was cooled to ambient temperature, poured into water and extracted with EtOAc, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (60% EtOAc in hexanes) to afford (S)-3-(4-bromo-2-fluoro-5-methylphenoxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one (420 mg, 0.880 mmol, 59.8% yield) as a tan solid.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b2684b9c488342a4b9add86e8fda3dc5
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754226B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes