Triethylamine → HCID 57717581, compound

HRID 1360500Notes

Reaction equation

HRID 1360500 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C:12]([CH3:32])([CH3:31])[CH2:13][C:14]1[N:15]([CH2:28][CH2:29][CH3:30])[N:16]=[C:17]2[C:26]=1[C:25]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:19]=[C:18]2[NH2:27].C(N(CC)CC)C>ClCCl>[NH2:27][C:18]1[C:17]2=[N:16][N:15]([CH2:28][CH2:29][CH3:30])[C:14]([CH2:13][C:12]([NH:11][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)([CH3:32])[CH3:31])=[C:26]2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 57717565HCID 57717565, compound

Product 1

HCID 57717581HCID 57717581, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nicotinoyl chloride hydrochloride (1.62 g, 9.08 mmol) was added to a stirred solution of 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 1.08 g, 3.63 mmol) and triethylamine (2.8 mL, 20 mmol) in dichloromethane (32.4 mL). After 2 h, the solution was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL). Concentrated hydrochloric acid (4 mL) was added and the solution was heated at reflux for 30 minutes, then was allowed to cool to ambient temperature. To the solution was added 2 M aqueous sodium carbonate until the pH was basic, then water was added. The mixture was extracted with chloroform four times. The organic layers were combined, dried over sodium sulfate, filtered, and concentrated to yield a brown oil that was purified by IFC (silica gel, elution with CMA in chloroform). The appropriate fractions were combined and concentrated to produce a yellow foam that was crystallized from ethyl acetate/hexanes. The solid was isolated by filtration and dried to yield 418 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]nicotinamide as a pale yellow solid, mp 203-205° C.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (20 mL)
  3. additionConcentrated hydrochloric acid (4 mL) was added
  4. temperaturethe solution was heated
  5. temperatureat reflux for 30 minutes
  6. additionTo the solution was added 2 M aqueous sodium carbonate until the pH
  7. additionwater was added
  8. extractionThe mixture was extracted with chloroform four times
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto yield a brown oil that
  13. customwas purified by IFC (silica gel, elution with CMA in chloroform)
  14. concentrationconcentrated
  15. customto produce a yellow foam that
  16. customwas crystallized from ethyl acetate/hexanes
  17. customThe solid was isolated by filtration
  18. customdried

Sources & evidence

ORD record
ord-d3c811ac021c4426b401bb65655902e8
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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