HCID 66958658, compound → HCID 57717585, compound

HRID 2283794Notes

Reaction equation

HRID 2283794 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH3:20])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.CO.[Pt](=O)=O>[NH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH3:20])[N:8]=[C:9]2[C:18]=1[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[N:11]=[C:10]2[NH2:19]

Participants

6

Reactant 1

HCID 66958658HCID 66958658, compound

Product 1

HCID 57717585HCID 57717585, compoundYield 90.8%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-(2-aminoethyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine dihydrochloride (7.20 g, 22.9 mmol) in trifluoroacetic acid (75 mL) was treated with platinum (IV) oxide (7.0 g) and shaken under hydrogen pressure (50 psi, 3.4×105 Pa) for 24 hours on a Parr apparatus. The reaction mixture was diluted with chloroform (50 mL) and methanol (25 mL) and filtered through a layer of CELITE filter agent. The filtrate was concentrated under reduced pressure. The residue was suspended in concentrated hydrochloric acid (5 mL), stirred for 2 hours, treated with 50% aqueous sodium hydroxide to adjust the pH to 13, and stirred at ambient temperature overnight. The mixture was diluted with water (100 mL) and was extracted with chloroform (5×150 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 5.10 g of 1-(2-aminoethyl)-2-methyl-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-c]quinolin-4-amine as an off-white foam.

Workup

  1. filtrationfiltered through a layer of CELITE filter agent
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. stirringstirred for 2 hours
  4. additiontreated with 50% aqueous sodium hydroxide
  5. stirringstirred at ambient temperature overnight
  6. additionThe mixture was diluted with water (100 mL)
  7. extractionwas extracted with chloroform (5×150 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d6afe851b9e4c8e84572135d7c9c197
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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