Water → HCID 22664816, compound

HRID 395336Notes

Reaction equation

HRID 395336 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-d7c580bb0ea6403187d16d61deef8695
Source dataset
uspto-grants-2003_08
Patent number
US06605617B2

Reaction notes

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