Water → HCID 178474193, compound

HRID 624794Notes

Reaction equation

HRID 624794 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:11][CH2:10]2)[N:5]2[N:12]=[CH:13][C:14](/[CH:15]=[C:16]3/[C:17](=[O:22])[NH:18][C:19](=[O:21])[NH:20]/3)=[C:4]2[N:3]=1.[NH2:23][C:24]1[CH:25]=[C:26]([NH:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:28][CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:9]1([NH:8][C:6]2[N:5]3[N:12]=[CH:13][C:14](/[CH:15]=[C:16]4\[NH:20][C:19](=[O:21])[NH:18][C:17]\4=[O:22])=[C:4]3[N:3]=[C:2]([NH:23][C:24]3[CH:25]=[C:26]([NH:30][C:31](=[O:33])[CH3:32])[CH:27]=[CH:28][CH:29]=3)[CH:7]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 7604m-AminoacetanilideHCID 10796Cesium carbonateHCID 178518477HCID 178518477, compound

Product 1

HCID 178474193HCID 178474193, compoundYield 12.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

(Z)-5-((5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (75 mg, 0.23 mmol) was suspended in 1,4-dioxane (1.6 mL). N-(3-aminophenyl)acetamide (52 mg, 0.35 mmol), Cs2CO3 (105 mg, 0.32 mmol), (±)-BINAP (9 mg, 0.06 mmol) and palladium(II) acetate (7 mg, 0.04 mmol) were then added. The mixture was sealed and irradiated at 120° C. for 30 min in the microwave. H2O (8 mL) was added and the precipitate was filtered off and dried. The crude residue was purified via flash column chromatography (2.5-3.5% MeOH/dichloromethane) to yield (Z)—N-(3-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)phenyl)acetamide (12 mg, 12%) as a bright yellow solid. LCMS (ES): >90% pure, m/z 433 [M+1]+.

Workup

  1. customThe mixture was sealed
  2. customirradiated at 120° C. for 30 min in the microwave
  3. filtrationthe precipitate was filtered off
  4. customdried
  5. customThe crude residue was purified via flash column chromatography (2.5-3.5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-736523388598470dad7e8dfa7be7f5aa
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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