Potassium Carbonate → HCID 18756085, compound

HRID 433895Notes

Reaction equation

HRID 433895 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[N:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([CH2:40][CH2:41][S:42]([NH2:45])(=[O:44])=[O:43])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>CS(C)=O>[Cl:17][C:6]1[N:5]=[C:4]([C:18]2[N:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[N:3]=[C:2]([NH:45][S:42]([CH2:41][CH2:40][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)(=[O:43])=[O:44])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11279505HCID 11279505, compoundHCID 17825700HCID 17825700, compound

Product 1

HCID 18756085HCID 18756085, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-[4,6-dichloro-5-(2-methoxyphenoxy)-2-pyrimidinyl] pyridazine, (0.06 g, 0.7 mmol) in dimethylsulfoxide (4 ml) was added potassium carbonate (0.13 g, 0.94 mmol) immediately followed by 2-(1-naphthyl) ethanesulfonamide (0.044 g, 0.18 mmol). The mixture was stirred vigorously for 72 hours at 90° C. and then quenched with hydrochloric acid solution (2 M, 4 ml). Ice-cold water (5 ml) was added and a white precipitate was observed. The resultant mixture was partitioned between water (10 ml) and dichloromethane (3×10 ml). The combined organic extracts were washed with water (3×10 ml), dried (magnesium sulfate) and concentrated under vacuum, yielding a yellow oil. Trituration with 1 ml of ice cold water, followed by filtration gave the title compound as a white solid (0.088 g), m.p. 191.5° C.

Workup

  1. customquenched with hydrochloric acid solution (2 M, 4 ml)
  2. additionIce-cold water (5 ml) was added
  3. customThe resultant mixture was partitioned between water (10 ml) and dichloromethane (3×10 ml)
  4. washThe combined organic extracts were washed with water (3×10 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under vacuum
  7. customyielding a yellow oil
  8. filtrationTrituration with 1 ml of ice cold water, followed by filtration

Sources & evidence

ORD record
ord-aea775fa6ed6477f9d71b1fe6d9d2a2c
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Reaction notes

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