Ethanol → HCID 18974894, compound

HRID 2393358Notes

Reaction equation

HRID 2393358 reaction equation
BrCC([N:5]1[C:14]2[N:10]([C:11]([CH3:15])=[N:12][N:13]=2)[C:9]2[CH:16]=[CH:17][CH:18]=[CH:19][C:8]=2[C:7]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=[N:6]1)=O.COC1[C:30]([NH2:35])=[CH:31][CH:32]=CC=1.[CH2:36]([OH:38])[CH3:37]>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:7]2[C:8]3[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=3[N:10]3[C:14]([N:5]([CH2:37][C:36](=[O:38])[NH:35][CH2:30][CH2:31][CH3:32])[N:6]=2)=[N:13][N:12]=[C:11]3[CH3:15])=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 70002-MethoxyanilineHCID 18974948HCID 18974948, compound

Product 1

HCID 18974894HCID 18974894, compound

Conditions

Temperature
80 °C

Procedure

4-Bromoacetyl-6-(4-chlorophenyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene (8 mg) obtained in Example 171 was suspended in ethanol and 2-anisidine (12.5 μl) was added. The mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Water (20 ml) was added to the residue and the mixture was extracted with ethyl acetate (20 ml). The organic layer was further washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by preparative thin-layer chromatography to give 2.4 mg of the title compound as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionWater (20 ml) was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate (20 ml)
  5. washThe organic layer was further washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-cb36be60f976412484c9c19b2d29e63c
Source dataset
uspto-grants-1998_09
Patent number
US05807850

Reaction notes

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