Potassium Carbonate → HCID 58645511, compound

HRID 545098Notes

Reaction equation

HRID 545098 reaction equation
Br[CH:2](Br)[C:3]([C:5]1[N:6]=[N:7][C:8]([O:15][CH2:16][CH3:17])=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=O.Cl.Cl.[N:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([NH2:28])[C:22]=1[NH2:29].C([O-])([O-])=O.[K+].[K+]>O.O1CCOCC1.[Cl-].[Na+].O>[CH2:16]([O:15][C:8]1[N:7]=[N:6][C:5]([C:3]2[N:29]=[C:22]3[N:21]=[CH:26][CH:25]=[C:24]([NH2:27])[C:23]3=[N:28][CH:2]=2)=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=1)[CH3:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 57446852HCID 57446852, compoundHCID 58645619HCID 58645619, compound

Product 1

HCID 58645511HCID 58645511, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve 2,2-dibromo-1-[6-ethoxy-4-(trifluoromethyl)pyridazin-3-yl]ethanone (5.45 g, 13.9 mmol), pyridine-2,3,4-triamine dihydrochloride (3.42 g, 17.4 mmol; prepared essentially as described by Kogl et al. (1948) Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 67:29-44) and K2CO3 (19.2 g, 139 mmol) in H2O (80 mL) and dioxane (40 mL). Heat the mixture at 100° C. for 3 hours. Cool and add brine (50 mL). Extract with EtOAc (3×50 mL). Combine, dry and evaporate the organic extracts. Purify by silica gel column chromatography eluting with CH2Cl2/MeOH (97/3) to yield two different regioisomers as a (2:1) mixture with the title compound being the major more polar isomer. LC/MS (MH+) 337.04.

Workup

  1. customprepared essentially
  2. temperatureCool
  3. extractionExtract with EtOAc (3×50 mL)
  4. customCombine, dry
  5. customevaporate the organic extracts
  6. customPurify by silica gel column chromatography
  7. washeluting with CH2Cl2/MeOH (97/3)

Sources & evidence

ORD record
ord-f5f4e19142b743fd81fb8af2faaefa6c
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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