Water → HCID 54767326, compound

HRID 1498609Notes

Reaction equation

HRID 1498609 reaction equation
Br[C:2]1[N:3]=[C:4]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[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)[CH:7]=1.[CH3:29][C:30]([OH:34])([C:32]#[CH:33])[CH3:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH:18]1([NH:17][C:15](=[O:16])[C:14]2[CH:21]=[CH:22][C:11]([C:8]3[N:6]4[CH:7]=[C:2]([C:33]#[C:32][C:30]([OH:34])([CH3:31])[CH3:29])[N:3]=[C:4]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])[C:5]4=[N:10][CH:9]=3)=[CH:12][CH:13]=2)[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 962WaterHCID 82582-Methyl-3-butyn-2-olHCID 2724141Tetrabutylammonium FluorideHCID 86692021HCID 86692021, compound

Product 1

HCID 54767326HCID 54767326, compoundYield 2.3%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 90 mg (203 μmol) 4-{6-bromo-8-[(4-hydroxybutyl)amino]imidazo[1,2-a]pyrazin-3-yl}-N-cyclopropylbenzamide which was prepared according to intermediate example 8a in 2.0 mL tetrahydrofuran were added 68.1 mg 2-methylbut-3-yn-2-ol, 1.0 mL tetrabutylammonium fluoride (1 molar in tetrahydrofuran) and 42.8 mg bis(triphenylphosphine)palladium (II) chloride. The mixture was subjected to microwave radiation for 2 hours at 130° C. Water was added and the mixture was extracted with dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 2.1 mg (2%) of the title compound.

Workup

  1. customfor 2 hours
  2. customat 130° C
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and removal of the solvent the residue
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-0b9d88c2493c46668e0b55a9c35c59e2
Source dataset
uspto-grants-2015_12
Patent number
US09199999B2

Reaction notes

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