Cesium carbonate → HCID 90052315, compound

HRID 2284780Notes

Reaction equation

HRID 2284780 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C@@H:19]([N:21]([CH3:30])[C:22](=[O:29])/[CH:23]=[CH:24]/[CH2:25][N:26]([CH3:28])[CH3:27])[CH3:20])=[CH:4][N:3]=1.[NH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:27][N:26]([CH3:28])[CH2:25]/[CH:24]=[CH:23]/[C:22]([N:21]([CH3:30])[C@@H:19]([CH3:20])[C:18]([NH:17][CH2:16][CH2:15][CH2:14][C:13]#[C:12][C:5]1[C:6]([NH:8][CH2:9][CH2:10][CH3:11])=[N:7][C:2]([NH:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[N:3][CH:4]=1)=[O:31])=[O:29]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 4082852-MorpholinoethylamineHCID 90052314HCID 90052314, compound

Product 1

HCID 90052315HCID 90052315, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To (S,E)-N-(1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)-4-(dimethylamino)-N-methyl-2-butenamide (L4, 30 mg), 4-(2-aminoethyl)morpholine (18 μL), tris(dibenzylideneacetone)dipalladium(0) (6.1 mg), 4,5′-bis(diphenylphosphino)-9,9′-dimethylxanthene (7.7 mg) and cesium carbonate (65 mg), 1,4-dioxane (2 mL) was added at room temperature, the reaction vessel was sealed, and then the mixture was stirred at 150° C. for 30 minutes by using a microwave reaction system. The reaction mixture was cooled to room temperature, then the insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 95% ethyl acetate/5% methanol) to obtain oily (S,E)-4-(dimethylamino)-N-methyl-N-(1-((5-(2-((2-morpholinoethyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)-2-butenamide (12-15, 2.9 mg).

Workup

  1. customthe reaction vessel was sealed
  2. customa microwave reaction system
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe insoluble matter was removed by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 95% ethyl acetate/5% methanol)

Sources & evidence

ORD record
ord-a44de07ecdce44338ccc626c187329b5
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…