Dimethylformamide → HCID 22676969, compound

HRID 1837401Notes

Reaction equation

HRID 1837401 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.Cl[C:18]1[N:23]2[N:24]=[CH:25][C:26]([N+:27]([O-:29])=[O:28])=[C:22]2[N:21]=[C:20]([CH3:30])[CH:19]=1.CN(C)C=O>O1CCOCC1>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:18]2[N:23]3[N:24]=[CH:25][C:26]([N+:27]([O-:29])=[O:28])=[C:22]3[N:21]=[C:20]([CH3:30])[CH:19]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 787361H-Imidazole-1-propanamineHCID 22676971HCID 22676971, compound

Product 1

HCID 22676969HCID 22676969, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2.88 g of 3-imidazol-1-ylpropylamine and 2.33 g of triethylamine in 20 cc of dioxane were introduced into a 100 cc three-necked round-bottomed flask equipped with a magnetic stirrer, a thermometer, a dropping funnel and a condenser. 4.5 g of 7-chloro-5-methyl-3-nitropyrazolo[1,5-a]pyrimidine in solution in 20 cc of dioxane and 5 cc of dimethylformamide were added dropwise. After 2 hours of stirring at room temperature, the precipitate was filtered off. It was washed with diisopropyl ether and dried under vacuum. This gave 7.2 g of crude product. This product was taken up under reflux in 28 cc of water, then filtered off at room temperature. This operation was repeated a second time. The product was washed with ethanol and with diisopropyl ether. This gave 4.1 g of (3-imidazol-1-ylpropyl)(5-methyl-3-nitropyrazolo[1,5-a]pyrimidin-7-yl)amine in the form of a beige powder, after drying under vacuum over phosphoric anhydride, with a yield of 65%.

Workup

  1. customequipped with a magnetic stirrer
  2. filtrationthe precipitate was filtered off
  3. washIt was washed with diisopropyl ether
  4. customdried under vacuum
  5. temperatureunder reflux in 28 cc of water
  6. filtrationfiltered off at room temperature
  7. washThe product was washed with ethanol and with diisopropyl ether
  8. dry with materialThis gave 4.1 g of (3-imidazol-1-ylpropyl)(5-methyl-3-nitropyrazolo[1,5-a]pyrimidin-7-yl)amine in the form of a beige powder, after drying under vacuum over phosphoric anhydride, with a yield of 65%

Sources & evidence

ORD record
ord-cbd4a941a0ea4c36b006243fe420a4d1
Source dataset
uspto-grants-2004_08
Patent number
US06783557B1

Reaction notes

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