Cesium carbonate → HCID 44124984, compound

HRID 1162498Notes

Reaction equation

HRID 1162498 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[N:17]=3)[N:14]=2)O1.[Cl:23][C:24]1[N:25]=[N:26][C:27](Cl)=[CH:28][C:29]=1[NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>[NH4+].[Cl-].O>[Cl:23][C:24]1[N:25]=[N:26][C:27]([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH:15]=[C:16]([NH:18][C:19](=[O:21])[CH3:20])[N:17]=3)[N:14]=2)=[CH:28][C:29]=1[NH:30][S:31]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)(=[O:32])=[O:33]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 57749426N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamideHCID 57749440N-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide

Product 1

HCID 44124984HCID 44124984, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a 50 mL round-bottomed flask was added N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (100 mg, 331 μmol), N-(3,6-dichloropyridazin-4-yl)-4-fluorobenzenesulfonamide (107 mg, 331 μmol), cesium carbonate (216 mg, 662 μmol), 662 μmol), dioxane (3 mL), water (0.5 mL). The reaction mixture was stirred at 90° C. for 2 h. The mixture was cooled down to room temperature. The reaction mixture was diluted with satd NH4Cl (2 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with satd NaCl (2 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography (15% MeOH/CH2Cl2) to give N-(6-(6-chloro-5-(4-fluorophenylsulfonamido)pyridazin-3-yl)imidazo[1,2-b]pyridazin-2-yl)acetamide (21 mg, 14% yield). MS (ESI positive ion) m/z: 461 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.13 (s, 3H) 7.36 (t, J=8.70 Hz, 3H) 7.53 (d, J=8.18 Hz, 1H) 7.82-8.00 (m, J=6.14 Hz, 2H) 8.05 (d, J=9.35 Hz, 1H) 8.29 (s, 1H)

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic extracts were washed with satd NaCl (2 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography (15% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-8bb1f21c7db3452183f4ac81525b3739
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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