Sodium Bicarbonate → HCID 66695611, compound

HRID 1773640Notes

Reaction equation

HRID 1773640 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:5]2[N:6]([C:8]([C:11]3[CH:22]=[CH:21][C:14]([C:15]([NH:17][CH:18]4[CH2:20][CH2:19]4)=[O:16])=[C:13]([CH3:23])[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[NH:29]1[C:33](B(O)O)=[CH:32][CH:31]=[N:30]1.C(=O)(O)[O-].[Na+]>C(O)C.C1(C)C=CC=CC=1>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[N:7]=[C:2]([C:31]5[NH:30][N:29]=[CH:33][CH:32]=5)[CH:3]=[C:4]([NH:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:5]4=[N:10][CH:9]=3)=[CH:12][C:13]=2[CH3:23])[CH2:20][CH2:19]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 112519791H-Pyrazole-5-boronic acidHCID 86705353HCID 86705353, compound

Product 1

HCID 66695611HCID 66695611, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 125 mg (314 μmol) 4-[6-chloro-8-(isobutylamino)imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropyl-2-methylbenzamide, which was prepared according to example 194a, 111 mg (942 μmol) 1H-pyrazol-5-yl boronic acid, 44 mg Tetrakis(triphenylphosphin)palladium in 2 mL of ethanol and 2 mL of toluene was added 0.63 mL of an aqueous 10% sodiumbicarbonate solution and the mixture was stirred at 120° C. for 2 hours under microwave irradiation. Then the mixture was filtered and concentrated and purified by chromatography to give 41 mg of the title compound.

Workup

  1. customwas prepared
  2. filtrationThen the mixture was filtered
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-5df5b5041f78452ca57d2d2c87447ece
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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