Diisopropylethylamine → HCID 86730250, compound

HRID 1850204Notes

Reaction equation

HRID 1850204 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.[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([CH:30]([NH2:32])[CH3:31])[CH:27]=[N:26]2)=[CH:21][CH:20]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH:29]=[C:28]([C@H:30]([NH:32][C:2]3[N:7]=[C:6]([N:8]4[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]4=[O:16])[CH:5]=[CH:4][N:3]=3)[CH3:31])[CH:27]=[N:26]2)=[CH:23][CH:24]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]2[CH:29]=[C:28]([C@@H:30]([NH:32][C:2]3[N:7]=[C:6]([N:8]4[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]4=[O:16])[CH:5]=[CH:4][N:3]=3)[CH3:31])[CH:27]=[N:26]2)=[CH:23][CH:24]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 16640664HCID 16640664, compoundHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 2

HCID 86730250HCID 86730250, compoundHCID 86730251HCID 86730251, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (98 mg, 0.41 mmol), 1-(1-(4-fluorophenyl)-1H-pyrazol-4-yl)ethanamine hydrochloride (502 mg, 2.08 mmol, 5.1 equiv) and iPr2NEt (0.637 mL, 3.65 mmol, 9.0 equiv) in DMSO (1.5 mL) was heated at 110° C. for 16 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)-3-(2-((R)-1-(1-(4-fluorophenyl)-1H-pyrazol-4-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one and (S)-3-(2-((S)-1-(1-(4-fluorophenyl)-1H-pyrazol-4-yl)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-8283e90b8843405a97199a1fa9f54fd4
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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