HCID 178418361, compound → HCID 178428507, compound

HRID 1837403Notes

Reaction equation

HRID 1837403 reaction equation
[Cl-:1].[OH:2][CH2:3][CH2:4][N+:5]1[CH:9]=[CH:8][N:7]([CH2:10][CH2:11][CH2:12][NH:13][C:14]2[N:19]3[N:20]=[CH:21][C:22]([N+:23]([O-])=O)=[C:18]3[N:17]=[C:16]([CH3:26])[CH:15]=2)[CH:6]=1.[H][H]>C(O)C.[Pd]>[ClH:1].[ClH:1].[Cl-:1].[NH2:23][C:22]1[CH:21]=[N:20][N:19]2[C:14]([NH:13][CH2:12][CH2:11][CH2:10][N:7]3[CH:8]=[CH:9][N+:5]([CH2:4][CH2:3][OH:2])=[CH:6]3)=[CH:15][C:16]([CH3:26])=[N:17][C:18]=12

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178428509HCID 178428509, compound

Product 1

HCID 178428507HCID 178428507, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3.5 g of 1-(2-hydroxyethyl)-3-[3-(5-methyl-3-nitropyrazolo[1,5-a]pyrimidin-7-ylamino)propyl]-3H-imidazol-1-ium chloride in 150 cc of ethanol and then 0.39 g of 5% palladium on carbon (containing 50% water) were introduced into a 250 cc hydrogenator. Between 11 and 12 bars' pressure of hydrogen were introduced into the reactor and the reaction medium was brought to 60° C. After 4 hours of reaction, the catalyst was filtered over Celite and a stream of gaseous hydrochloric acid was passed through the filtrate. The reaction medium was poured into 100 cc of diisopropyl ether. After stirring, the precipitate was filtered off. It was washed with diisopropyl ether and dried under vacuum over phosphoric anhydride. This gave 3.3 g of a highly hygroscopic product. A 3% aqueous solution of this product was formed, and was lyophilized. The resulting solid was taken up at reflux in 30 cc of absolute ethanol. This gives 2.25 g of 3-[3-(3-amino-5-methylpyrazolo[1,5-a]pyrimdin-7-ylamino)propyl]-1-(2-hydroxyethyl)-3H-imidazol-1-ium chloride in the form of the dihydrochloride, after drying under vacuum over phosphoric anhydride, with a yield of 85%, whose analysis calculated for C15H22N7OCl, 2HCl (MW=424.76 g) was as follows:

Workup

  1. customwas brought to 60° C
  2. customAfter 4 hours of reaction
  3. filtrationthe catalyst was filtered over Celite
  4. additionThe reaction medium was poured into 100 cc of diisopropyl ether
  5. filtrationthe precipitate was filtered off
  6. washIt was washed with diisopropyl ether
  7. dry with materialdried under vacuum over phosphoric anhydride

Sources & evidence

ORD record
ord-1a630bd554d44afca6d426bc673d2788
Source dataset
uspto-grants-2004_08
Patent number
US06783557B1

Reaction notes

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