Hydrogen Peroxide → HCID 86675895, compound

HRID 710024Notes

Reaction equation

HRID 710024 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH2:30][CH2:29]2)=[C:17]([NH:19][C:20]([C:22]2[O:23][C:24](Br)=[CH:25][CH:26]=2)=[O:21])[CH:18]=1)=[O:12].C([O-])([O-])=O.[K+].[K+].OO.O.[CH3:50][C:51](N(C)C)=O>CS(C)=O.[C-]#N.[C-]#N.[Zn+2].[Zn].CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd]>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH2:30][CH2:29]2)=[C:17]([NH:19][C:20]([C:22]2[O:23][C:24]([C:50]#[CH:51])=[CH:25][CH:26]=2)=[O:21])[CH:18]=1)=[O:12]

Participants

10

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 71234026HCID 71234026, compound

Product 1

HCID 86675895HCID 86675895, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

Furan-2,5-dicarboxylic acid 2-amide 5-{[5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide} (compound no. 216) was prepared as follows: 5-Bromo-furan-2-carboxylic acid [5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide (0.1 g, 0.164 mmol), Zn(CN)2 (0.038 g, 0.33 mmol), Zn (2.1 mg, 0.033 mmol) were taken in DMA (5.0 mL) and the solution was degassed for 5 min. Pd(t-Bu3P)2 (8.0 mg, 0.016 mmol) was added to this, and the solution was degassed and nitrogen purged again. The reaction mixture was stirred at 85° C. under nitrogen for 5 h. It was cooled, dissolved in MeOH and purified on preparative HPLC using water/methanol as eluent to the intermediate nitrile (0.07 g, 79%). The above nitrile (0.05 g, 0.09 mmol) was taken in DMSO (2.0 mL). K2CO3 (0.074 mg, 0.54 mmol) was added to this followed by H2O2 (0.031 g, 0.27 mmol) and the reaction was stirred at room temperature for 4 h. LC-MS indicated the completion of the reaction. Water (2.0 mL) was added and the product crashed out. It was filtered and dried to give the desired product (0.025 g, 47%).

Workup

  1. customthe solution was degassed for 5 min
  2. customwas degassed
  3. customnitrogen purged again
  4. temperatureIt was cooled
  5. dissolutiondissolved in MeOH
  6. custompurified on preparative HPLC
  7. stirringthe reaction was stirred at room temperature for 4 h
  8. customthe completion of the reaction
  9. filtrationIt was filtered
  10. customdried

Sources & evidence

ORD record
ord-bba390cdfe3645c29aaea4ebb98cc875
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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