Acetonitrile → (5-(1h-Indazol-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-(methylsulfonyl)piperazin-1-yl)methanone

HRID 1692801Notes

Reaction equation

HRID 1692801 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]3)=[O:12])=[N:8][C:6]=2[N:7]=1.B(O)(O)[C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1[CH:32]=[N:33][NH:34]2.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH:34]1[C:35]2[C:31](=[C:30]([C:2]3[N:3]=[C:4]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:5]4[S:10][C:9]([C:11]([N:13]5[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]5)=[O:12])=[N:8][C:6]=4[N:7]=3)[CH:38]=[CH:37][CH:36]=2)[CH:32]=[N:33]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 441183101H-Indazole-4-boronic acidHCID 86630083(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-methylsulfonylpiperazin-1-yl)methanone

Product 1

HCID 25254936(5-(1h-Indazol-4-yl)-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-(methylsulfonyl)piperazin-1-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)(4-methylsulfonylpiperazin-1-yl)methanone, 1H-indazol-4-yl-4-boronic acid (2.5 eq), and trans-dichlorobis(triphenylphosphine)palladium(II) (0.1 eq) were slurried with equal parts 1M sodium carbonate aqueous solution (3 eq) and acetonitrile. The solution was microwaved at 140° C. for 10 minutes. Water was added and the solution was filtered. The resulting precipitate was washed with methylene chloride and the organic layer was purified by silica gel chromatography followed by reverse phase silica gel chromatography to give the product 141.

Workup

  1. customThe solution was microwaved at 140° C. for 10 minutes
  2. filtrationthe solution was filtered
  3. washThe resulting precipitate was washed with methylene chloride
  4. customthe organic layer was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6f901462c59e4224ae163e8e7bd68547
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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