HCID 57717543, compound → 1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1360414Notes

Reaction equation

HRID 1360414 reaction equation
C([N:8]1[C:20]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:19]2[C:10]([C:11]([NH2:25])=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=32)=[N:9]1)C1C=CC=CC=1>Br>[CH3:23][CH:22]([CH3:24])[CH2:21][C:20]1[NH:8][N:9]=[C:10]2[C:19]=1[C:18]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:12]=[C:11]2[NH2:25]

Participants

3

Reactant 1

HCID 57717543HCID 57717543, compound

Product 1

HCID 577175171-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amineYield 25.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
150 °C

Procedure

Hydrogen bromide (10 mL of 30% by weight in acetic acid) and 2-benzyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (0.75 g, 2.27 mmol) were combined in a TEFLON-lined Parr vessel and heated at 150° C. for 24 hours and then allowed to cool to ambient temperature over five hours. The reaction was filtered to remove a solid, and the filtrate was adjusted to pH 7 with the addition of 50% sodium hydroxide and 2M aqueous sodium carbonate. A precipitate formed and was isolated by filtration, washed with water, and air-dried. The solid was purified by chromatography on a HORIZON HPFC system (25+M cartridge, eluting with chloroform/CMA in a gradient from 80:20 to 40:60) followed by recrystallization from acetonitrile (19 mL/g) and a small amount of methanol. The crystals were isolated by filtration, washed with acetonitrile, and dried for 36 hours in a vacuum oven at 65° C. to provide 139 mg of 1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine as small, pale orange needles, mp 248-249° C.

Workup

  1. temperatureto cool to ambient temperature over five hours
  2. filtrationThe reaction was filtered
  3. customto remove a solid
  4. additionthe filtrate was adjusted to pH 7 with the addition of 50% sodium hydroxide and 2M aqueous sodium carbonate
  5. customA precipitate formed
  6. customwas isolated by filtration
  7. washwashed with water
  8. customair-dried
  9. customThe solid was purified by chromatography on a HORIZON HPFC system (25+M cartridge
  10. washeluting with chloroform/CMA in a gradient from 80:20 to 40:60)
  11. customfollowed by recrystallization from acetonitrile (19 mL/g)
  12. customThe crystals were isolated by filtration
  13. washwashed with acetonitrile
  14. customdried for 36 hours in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-a26ff3c9d7b344d0a0fc07c9765501fb
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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