1-(4-Chlorophenyl)ethylamine → HCID 86730221, compound

HRID 1850191Notes

Reaction equation

HRID 1850191 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([NH2:26])[CH3:25])=[CH:20][CH:19]=1>CS(C)=O.CCOC(C)=O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@H:24]([NH:26][C:2]2[N:7]=[C:6]([N:8]3[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]3=[O:16])[CH:5]=[CH:4][N:3]=2)[CH3:25])=[CH:20][CH:19]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:2]2[N:7]=[C:6]([N:8]3[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]3=[O:16])[CH:5]=[CH:4][N:3]=2)[CH3:25])=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 978031-(4-Chlorophenyl)ethylamineHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 2

HCID 86730221HCID 86730221, compoundHCID 86730222HCID 86730222, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (96 mg, 0.40 mmol) and 1-(4-chlorophenyl)ethanamine (204 mg, 1.31 mmol, 3.3 equiv) in DMSO (1 mL) was heated at 110° C. for 3 h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 50%) provided (S)-3-(2-((R)-1-(4-chlorophenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one and (S)-3-(2-((S)-1-(4-chlorophenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one.

Workup

  1. washwashed with water (30 mL)
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc (3×8 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bd5f44aeaeb4cc8904fcd338cb86e2b
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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