Morpholine → HCID 117833381, compound

HRID 2169757Notes

Reaction equation

HRID 2169757 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[C:12](=[O:20])[N:13]([CH3:19])[N:14]=[CH:15][C:16]=2[O:17]C)[CH:3]=1.N1CCOCC1>O>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH:11]2[C:16](=[O:17])[CH:15]=[N:14][N:13]([CH3:19])[C:12]2=[O:20])[CH:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 89876268HCID 89876268, compound

Product 1

HCID 117833381HCID 117833381, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(3-Chloro-indol-1-yl)-5-methoxy-2-methyl-2H-pyridazin-3-one (1.70 g, 5.87 mmol) and morpholine (8 ml) is heated to 140° C. under microwave irradiation for 10 min. The mixture is allowed to cool then evaporated under reduced pressure to remove most of the morpholine. The residue is stirred with 1:1 v/v glacial AcOH:DCM (100 ml) to give a free-flowing semi-solid. Volatiles are removed in-vacuo and the solid obtained slurried with water. The solid is recovered by filtration under reduced pressure and dried at 1 mBar and 60° C. to give the title compound as a beige solid, 1.54 g, 95% yield. 1H nmr (DMSO-d6) δ (ppm) 7.89 (1H, s), 7.57-7.50 (2H, m), 7.24-7.17 (2H, m), 7.12-7.06 (1H, m), 3.66 (3H, s)

Workup

  1. temperatureto cool
  2. customthen evaporated under reduced pressure
  3. customto remove most of the morpholine
  4. customDCM (100 ml) to give a free-flowing semi-solid
  5. customVolatiles are removed in-vacuo
  6. customthe solid obtained
  7. filtrationThe solid is recovered by filtration under reduced pressure
  8. customdried at 1 mBar and 60° C.

Sources & evidence

ORD record
ord-07b43899a0f7409882846f3f3377fa1a
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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