5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine → (S)-3-(2-((S)-1-(4-((5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

HRID 1850223Notes

Reaction equation

HRID 1850223 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]3=[O:26])[CH:15]=[CH:14][N:13]=2)[CH3:10])=[CH:5][CH:4]=1.[N:27]1[CH:28]=[CH:29][N:30]2[CH2:35][CH2:34][NH:33][CH2:32][C:31]=12>CS(C)=O.CCOC(C)=O>[N:27]1[CH:28]=[CH:29][N:30]2[CH2:35][CH2:34][N:33]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]4[N:17]=[C:16]([N:18]5[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]5=[O:26])[CH:15]=[CH:14][N:13]=4)[CH3:10])=[CH:5][CH:4]=3)[CH2:32][C:31]=12

Participants

5

Reactant 2

HCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazineHCID 86730209HCID 86730209, compound

Product 1

HCID 86730278(S)-3-(2-((S)-1-(4-((5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-oneYield 62.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-((S)-1-(4-(chloromethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (75 mg, 0.2 mmol) and 5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine (25 mg, 0.2 mmol) in DMSO (2 mL) was heated at 80° C. for 16 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL). After separation, the aqueous phase was washed with EtOAc (2×15 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (MeOH in CH2Cl2 0 to 10%) provided (S)-3-(2-((S)-1-(4-((5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl)methyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (58 mg, white solid) in 62.8% yield.

Workup

  1. washwashed with water (20 mL)
  2. customAfter separation
  3. washthe aqueous phase was washed with EtOAc (2×15 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-30e20003c9b04b9aa1a18bdbaaa65d36
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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