Morpholine → HCID 86730406, compound

HRID 871153Notes

Reaction equation

HRID 871153 reaction equation
Cl[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][C:16]=3[CH3:17])=[C:5]2[O:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:17][C:16]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:2]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[N:3][O:4][C:5]=12

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 86730407HCID 86730407, compound

Product 1

HCID 86730406HCID 86730406, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 3-chloro-7-(4-methylpyridin-3-yl)isoxazolo[4,5-b]pyridine (0.0069 g, 0.028 mmol) and morpholine (0.025 ml, 0.281 mmol) in DMSO (Volume: 0.100 ml) was added cesium carbonate (0.027 g, 0.084 mmol). The vial was sealed, heated at 90° C. for 4 hr, and then allowed to cool to room temperature. The reaction mixture was filtered through a disposable fritted funnel and the filter cake washed with CH2Cl2. The solvent was concentrated to afford a yellow liquid, which was further dried under high vacuum overnight. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (4 g column, 18 mL/min, 70-100% EtOAc in hexanes over 14 min, tr=4.5 min) gave 7-(4-methylpyridin-3-yl)-3-morpholinoisoxazolo[4,5-b]pyridine (6.5 mg, 0.021 mmol, 76% yield) as a white solid. ESI MS (M+H)+=297.2. HPLC Peak tr=1.56 minutes. Purity=97%. HPLC Conditions: C.

Workup

  1. customThe vial was sealed
  2. temperatureto cool to room temperature
  3. filtrationThe reaction mixture was filtered through a disposable fritted funnel
  4. washthe filter cake washed with CH2Cl2
  5. concentrationThe solvent was concentrated
  6. customto afford a yellow liquid, which
  7. customwas further dried under high vacuum overnight
  8. dissolutionThe crude material was dissolved in a minimal amount of CH2Cl2
  9. customto be chromatographed
  10. customPurification of the crude material by silica gel chromatography
  11. customan ISCO machine (4 g column, 18 mL/min, 70-100% EtOAc in hexanes over 14 min, tr=4.5 min)

Sources & evidence

ORD record
ord-57ca7316e51d4645b038182246ef60c3
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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