Water → HCID 21822190, compound

HRID 517801Notes

Reaction equation

HRID 517801 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:14][C:15]1[N:19]2[N:20]=[C:21](Cl)[CH:22]=[CH:23][C:18]2=[N:17][N:16]=1.O>CN(C)C=O>[Cl:14][C:15]1[N:19]2[N:20]=[C:21]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:22]=[CH:23][C:18]2=[N:17][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 14823463,6-Dichloro[1,2,4]triazolo[4,3-b]pyridazine

Product 1

HCID 21822190HCID 21822190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

0.9 cm3 of morpholine and 1.4 cm3 of triethylamine are added to a solution of 1.89 g of commercial 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine in 20 cm3 of N,N-dimethylformamide. The reaction is stirred at 20° C. for 19 h. 60 cm3 of water are added and the mixture is extracted with ethyl acetate. The organic phase is washed with water and with brine and then dried over magnesium sulphate and concentrated to dryness, to give a beige solid. The latter is chromatographed by solid deposit on a Merck cartridge of 70 g of silica 15-40 μm, elution being carried out with a gradient of 100% dichloromethane to 95/5 dichloromethane/methanol. 1.97 g of 3-chloro-6-(morpholin-4-yl)[1,2,4]triazolo[4,3-b]pyridazine are obtained in the form of a very pale yellow solid, the characteristics of which are as follows:

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water and with brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness
  5. customto give a beige solid
  6. customThe latter is chromatographed by solid deposit on a Merck cartridge of 70 g of silica 15-40 μm, elution

Sources & evidence

ORD record
ord-9e44be1037cb41d6a48e7b7ee7bb1bd3
Source dataset
uspto-grants-2015_08
Patent number
US09115134B2

Reaction notes

Loading…