Hydrochloric Acid → HCID 66958866, compound

HRID 2283887Notes

Reaction equation

HRID 2283887 reaction equation
Cl.[NH2:2][C:3]1[C:12]2=[N:13][N:14]([CH2:26][CH2:27][CH3:28])[C:15]([CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)=[C:11]2[C:10]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=2[N:4]=1>C(O)C>[NH2:18][CH2:17][CH2:16][C:15]1[N:14]([CH2:26][CH2:27][CH3:28])[N:13]=[C:12]2[C:11]=1[C:10]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[N:4]=[C:3]2[NH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66958887HCID 66958887, compound

Product 1

HCID 66958866HCID 66958866, compoundYield 126.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydrochloric acid (3 mL of 2.7 M in ethanol) was added to a suspension of tert-butyl 2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]-1,8-naphthyridin-1-yl)ethylcarbamate (0.52 g) in ethanol (10 mL). The mixture was heated at 80° C. for about 1 hour and then concentrated under reduced pressure. The residue was partitioned between water (50 mL) and dichloromethane (30 mL). The layers were separated. The aqueous layer was made basic with ammonium hydroxide and then extracted with dichloromethane (2×50 mL). The combined organics were washed with brine (1×50 mL), dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide 0.29 g of crude product as a white solid. The reaction was repeated using 2.05 g of starting material to provide 1.18 g of crude product as a white solid. The two lots were combined and purified by chromatography on a HORIZON HPFC system (silica gel eluting with a gradient of 20-60% of 80:20 CMA:chloroform in chloroform) to provide 0.48 g of 1-(2-aminoethyl)-2-propyl-2H-pyrazolo[3,4-c]-1,8-naphthyridin-4-amine as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water (50 mL) and dichloromethane (30 mL)
  3. customThe layers were separated
  4. extractionextracted with dichloromethane (2×50 mL)
  5. washThe combined organics were washed with brine (1×50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto provide 0.29 g of crude product as a white solid
  10. customto provide 1.18 g of crude product as a white solid
  11. custompurified by chromatography on a HORIZON HPFC system (silica gel eluting with a gradient of 20-60% of 80:20 CMA

Sources & evidence

ORD record
ord-edd7a2f619db49f192087d3d5e6f539a
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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