Potassium Carbonate → 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl morpholine-4-carboxylate

HRID 1039591Notes

Reaction equation

HRID 1039591 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[C:4]([OH:19])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(C(C)=O)C(C)C>[N:26]1([C:32]([O:19][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=2[O:8][C:9]2[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=2[CH:16]2[CH2:18][CH2:17]2)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 848104-Morpholinecarbonyl chlorideHCID 178424441HCID 178424441, compound

Product 1

HCID 230138546-Chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-yl morpholine-4-carboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To 6.50 g (23.5 mmol) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol were added 39 g of methyl isobutyl ketone and 3.57 g (25.9 mmol) of potassium carbonate, and the resultant mixture was stirred at 50° C. To the mixture was added dropwise 3.87 g (25.9 mmol) of morpholinecarbonyl chloride over one hour. The reaction mixture was subjected to reaction at 50° C. for 4 hours. After completion of the reaction, the resultant opaque mixture was subjected to filtration, and washed with methyl isobutyl ketone, and then the resultant organic phase was quantitatively determined by an HPLC internal standard analysis method, which showed that 9.00 g of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl morpholine-4-carboxylate (yield: 98%) was obtained.

Workup

  1. customThe reaction mixture was subjected to reaction at 50° C. for 4 hours
  2. customAfter completion of the reaction
  3. filtrationthe resultant opaque mixture was subjected to filtration
  4. washwashed with methyl isobutyl ketone

Sources & evidence

ORD record
ord-2f469088143c43e4916352cbd40d45db
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

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