Potassium Hydroxide → HCID 57717620, compound

HRID 1360530Notes

Reaction equation

HRID 1360530 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][C:10]2[N:11]([CH2:38][CH2:39][CH3:40])[N:12]=[C:13]3[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=[C:14]3[N:23](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[O:4][N:3]=1.[OH-].[K+]>Cl.C(O)C.O.[OH-].[K+]>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][C:10]2[N:11]([CH2:38][CH2:39][CH3:40])[N:12]=[C:13]3[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=[C:14]3[NH2:23])[O:4][N:3]=1

Participants

7

Reactant 2

HCID 14797Potassium HydroxideHCID 66958384HCID 66958384, compound

Product 1

HCID 57717620HCID 57717620, compoundYield 41.1%

Reagents, catalysts & solvents 4

HCID 14797Potassium HydroxideCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of di(tert-butyl) 1-[3-(3-methylisoxazol-5-yl)propyl]-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-ylimidodicarbonate (0.471 g, 0.856 mmol) in 6 M HCl in ethanol (5 mL) was heated at 60° C. for 1 hour. The solution was allowed to cool to room temperature, then was concentrated under reduced pressure to yield an oil that was dissolved in water (20 mL). The solution was adjusted to pH 12 with a few drops of 50% aqueous potassium hydroxide and then to pH 14 with 1 M aqueous potassium hydroxide. A precipitate formed that was isolated by filtration and crystallized from ethyl acetate/hexanes. The crystals were isolated by filtration and dried under vacuum at 70° C. to afford 0.123 g 1-[3-(3-methylisoxazol-5-yl)propyl]-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine as white needles, mp 183.0-184.0° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto yield an oil that
  3. customA precipitate formed
  4. customthat was isolated by filtration
  5. customcrystallized from ethyl acetate/hexanes
  6. customThe crystals were isolated by filtration
  7. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-d7138d59f0d147fbb333c1bed3d4c431
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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