Water → HCID 22664816, compound

HRID 392611Notes

Reaction equation

HRID 392611 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[H-].[Na+].[NH2:12][C:13]1[C:18]([C:19]#[N:20])=[C:17](F)[CH:16]=[CH:15][CH:14]=1.O>CN1C(=O)CCC1>[NH2:12][C:13]1[C:18]([C:19]#[N:20])=[C:17]([O:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 611632-MorpholinoethanolHCID 5226592-Amino-6-fluorobenzonitrile

Product 1

HCID 22664816HCID 22664816, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
100 °C

Procedure

4-(Hydroxyethyl)morpholine (1.02 eq) was added to NaH (1.2 eq) in NMP. After 10 minutes, 6-amino-2-fluorobenzenecarbonitrile (1.0 eq) was added in NMP. The resulting mixture was heated at 100° C. for 1 hour. The mixture was then cooled and poured into H2O. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a yield a brown gum. The crude material was purified by silica gel chromatography (5:1:95 MeOH:Et3N:EtOAc) to give the desired product. LC/MS m/z 248.3 (MH+), Rf 1.26 minutes.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to
  7. customa yield a brown gum
  8. customThe crude material was purified by silica gel chromatography (5:1:95 MeOH:Et3N:EtOAc)

Sources & evidence

ORD record
ord-dd943701f37f417cb8fed7a50b3c523c
Source dataset
uspto-grants-2004_10
Patent number
US06800760B2

Reaction notes

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