Cyclopropylamine → HCID 22320280, compound

HRID 498010Notes

Reaction equation

HRID 498010 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[CH:22]1([NH2:25])[CH2:24][CH2:23]1>O1CCCC1>[CH:22]1([NH:25][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]3[N:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)[N:13]=[C:14]([CH3:15])[C:3]=23)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320280HCID 22320280, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (0.7 g, 2.37 mmol) and cyclopropylamine (0.7 g, 73.6 mmol) in tetrahydrofuran (20 mL) was heated under reflux at 100° C. overnight in a sealed stainless tube. The solution was cooled to room temperature, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform:methanol=93:7) to give N-cyclopropyl-N-[3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolin-4-yl]amine. To a solution of the compound above in ethanol (10 mL), a saturated hydrochloric acid/ethanol solution (10 mL) was added and the solvent was evaporated under reduced pressure. The residue thus obtained was recrystallized from methanol/ethyl acetate to give the title compound (0.52 g, 56% yield).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by silica gel column chromatography (chloroform:methanol=93:7)

Sources & evidence

ORD record
ord-5202f0381cb84963a32316e55bdf20a4
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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