Diisopropylethylamine → HCID 86730283, compound

HRID 1850229Notes

Reaction equation

HRID 1850229 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.[F:17][C:18]1[CH:33]=[CH:32][C:21]([O:22][C:23]2[N:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C>CS(C)=O>[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:22][C:23]2[N:28]=[CH:27][C:26]([C@@H:29]([NH:31][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)[CH3:30])=[CH:25][CH:24]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81899864HCID 81899864, compoundHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 1

HCID 86730283HCID 86730283, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
107.5 °C

Procedure

To (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (28 mg, 0.116 mmol) was added (S)-1-(6-(4-fluorophenoxy)pyridin-3-yl)ethanamine (46.7 mg, 0.174 mmol), DMSO (0.6 ml) and Hunig's Base (0.071 ml, 0.406 mmol). The reaction was heated at 105-110° C. for 24 hours or until done by LCMS. The reaction was let cool, 0.5 ml of DMSO was added, filtered, purified by prep LC and lyophilized to give 7.1 mg of (S)-3-(2-((S)-1-(6-(4-fluorophenoxy)pyridin-3-yl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one as the TFA Salt. LCMS m/z 438.2 (M+H)+, Rt 0.82 min.

Workup

  1. temperatureThe reaction was let cool
  2. filtrationfiltered
  3. custompurified by prep LC

Sources & evidence

ORD record
ord-3f745b5d88dd484b9b8b6cb68707b0d5
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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