Dimethylformamide → HCID 178439451, compound

HRID 1357239Notes

Reaction equation

HRID 1357239 reaction equation
[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][NH:17][C:18]([C:20]1[CH:21]=[N:22][N:23]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]=1[CH2:25][CH2:26][CH3:27])=[O:19])=[CH:7]2.[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].CN(C=O)C>O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:36][N:35]=[N:34][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][NH:17][C:18]([C:20]1[CH:21]=[N:22][N:23]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:24]=1[CH2:25][CH2:26][CH3:27])=[O:19])=[CH:7]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium Chloride3×HCID 33557Sodium Azide3×HCID 12083562HCID 12083562, compound

Product 1

HCID 178439451HCID 178439451, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-phenyl-5-propyl-1H-pyrazole-4-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-amide (0.15 g, 0.3 mmol), prepared in the previous step, sodium azide (0.059 g, 0.9 mmol), ammonium chloride (0.048 g, 0.9 mmol) and 10 mL of DMF was stirred at 100° C. for 1.5 h. By TLC starting material remained. Additional sodium azide (0.059 g, 0.9 mmol) and ammonium chloride (0.048 g, 0.9 mmol) were added and the reaction stirred at 100° C. for 2 h. Again by TLC starting material remained. Additional sodium azide (0.059 g, 0.9 mmol) and ammonium chloride (0.048 g, 0.9 mmol) were added and the reaction stirred at 100° C. for 5 h. The reaction was diluted with water and extracted four times with ethyl acetate. The organic layers were combined and acidified with ˜3 mL 1N HCl. The mixture was swirled for one minute and then the solution was dried (MgSO4) and filtered. The solvent was removed under reduced pressure and the resulting residue was taken up in 20 mL of water. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (0.107 g, 65%) as a tan solid, mp 219-220° C.

Workup

  1. stirringthe reaction stirred at 100° C. for 2 h
  2. stirringthe reaction stirred at 100° C. for 5 h
  3. extractionextracted four times with ethyl acetate
  4. waitThe mixture was swirled for one minute
  5. dry with materialthe solution was dried (MgSO4)
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customThe solid that formed
  9. filtrationwas collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-8dcbcfdf0974472c8356db3079d85d6c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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