1-(1-Phenyl-1H-pyrazol-4-yl)ethan-1-amine → HCID 86730235, compound

HRID 1850198Notes

Reaction equation

HRID 1850198 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.[C:17]1([N:23]2[CH:27]=[C:26]([CH:28]([NH2:30])[CH3:29])[CH:25]=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C@@H:28]([C:26]2[CH:25]=[N:24][N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:27]=2)[CH3:29])[N:7]=1)([CH3:15])[CH3:14].[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:30][C@H:28]([C:26]2[CH:25]=[N:24][N:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:27]=2)[CH3:29])[N:7]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 431400971-(1-Phenyl-1H-pyrazol-4-yl)ethan-1-amineHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 2

HCID 86730235HCID 86730235, compoundHCID 86730236HCID 86730236, 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-(1-phenyl-1H-pyrazol-4-yl)ethanamine (387 mg, 2.97 mmol, 5.2 equiv) in DMSO (1.5 mL) was heated at 110° C. for 1½ 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 20 to 80%) provided (S)-4-isopropyl-3-(2-((R)-1-(1-phenyl-1H-pyrazol-4-yl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one and (S)-4-isopropyl-3-(2-((S)-1-(1-phenyl-1H-pyrazol-4-yl)ethylamino)pyrimidin-4-yl)oxazolidin-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-3afefe2e654646008cc2d787c022fc2c
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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