Ethanol → HCID 66691992, compound

HRID 1773639Notes

Reaction equation

HRID 1773639 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:23][CH2:24][C@@H:25]([C@H:27]2[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]2)[OH:26])[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])=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.B(O)O.C(=O)(O)[O-].[Na+].[CH2:42](O)[CH3:43]>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:5]5[N:6]([CH3:8])[N:7]=[CH:43][CH:42]=5)[CH:3]=[C:4]([NH:23][CH2:24][C@@H:25]([C@H:27]5[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28]5)[OH:26])[C:5]4=[N:10][CH:9]=3)=[CH:12][CH:13]=2)[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 702EthanolHCID 61668Boronic AcidHCID 516892Sodium BicarbonateHCID 86705352HCID 86705352, compound

Product 1

HCID 66691992HCID 66691992, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 52 mg (94 mot) 4-[6-chloro-8-({(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl}amino)imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropylbenzamide which was prepared according to intermediate example 192a, 33 mg 1-methyl-1H-pyrazol-5-yl) boronic acid, 6.5 mg tetrakis(triphenylphosphin)palladium in 1 mL of ethanol and 1 mL of toluene was added 0.26 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, the solvent was removed and the residue was purified by chromatography to give 36 mg of the title compounds.

Workup

  1. customwas prepared
  2. filtrationThen the mixture was filtered
  3. customthe solvent was removed
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-4ef3a23648524d3f944bba87187a0d5b
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

Loading…