Cyclopropanecarbonyl chloride → HCID 69583606, compound

HRID 2213076Notes

Reaction equation

HRID 2213076 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([C:17]2[CH:18]=[C:19]3[C:25]([NH2:26])=[N:24][NH:23][C:20]3=[CH:21][N:22]=2)[CH:8]=1>N1C=CC=CC=1>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]([C:17]2[CH:18]=[CH:19][C:20]3[NH:23][N:24]=[C:25]([NH:26][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[C:21]=3[N:22]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 21956505HCID 21956505, compound

Product 1

HCID 69583606HCID 69583606, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropane carbonyl chloride (168 mg, 1.602 mmol) was added to a stirred solution of 5-(quinolin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-ylamine (200 mg, 0.766 mmol) in anhydrous pyridine (5 mL) and the reaction was heated under reflux for 16 hours. The solvent was then removed in vacuo and the residue re-evaporated from water (10 mL) to yield a solid. This was triturated with saturated aqueous sodium bicarbonate solution and the mixture then left to stand for 0.5 hour until the pH stabilised at pH 9–10. The resulting solid was then collected by filtration, washed with water (3×25 mL) and dried in vacuo. This material was then stirred in piperidine (3 mL) at room temperature for 2 hours. The piperidine was evaporated and the residue triturated with water (5 mL) and with methanol (5 mL) to afford the title compound as a solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 16 hours
  3. customThe solvent was then removed in vacuo
  4. customthe residue re-evaporated from water (10 mL)
  5. customto yield a solid
  6. customThis was triturated with saturated aqueous sodium bicarbonate solution
  7. waitthe mixture then left
  8. filtrationThe resulting solid was then collected by filtration
  9. washwashed with water (3×25 mL)
  10. customdried in vacuo
  11. customThe piperidine was evaporated
  12. customthe residue triturated with water (5 mL) and with methanol (5 mL)

Sources & evidence

ORD record
ord-f9b152b1fdc64164b882c0ac17fdf105
Source dataset
uspto-grants-2006_09
Patent number
US07105532B2

Reaction notes

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