Triethylamine → HCID 57717538, compound

HRID 1984530Notes

Reaction equation

HRID 1984530 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[C:21]([CH2:22][CH:23]([CH3:25])[CH3:24])=[C:20]2[C:11]([C:12]([NH2:26])=[N:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=32)=[N:10]1.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>ClCCl>[CH2:22]([C:21]1[N:9]([CH3:8])[N:10]=[C:11]2[C:20]=1[C:19]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:13]=[C:12]2[NH:26][C:28](=[O:29])[O:30][CH2:31][CH3:32])[CH:23]([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 669586022-Methyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 57717538HCID 57717538, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

Triethylamine (0.49 mL, 3.53 mmol) was added to a suspension of 2-methyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 3) (0.75 g, 2.95 mmol) in dichloromethane (30 mL) and cooled to 4° C. Ethyl chloroformate (0.352 g, 3.24 mmol) was added in dichloromethane (5 mL) dropwise over 5 minutes to the reaction mixture and maintained at ambient temperature for 16 hours. The reaction mixture was diluted with dichloromethane (25 mL) and washed sequentially with water (25 mL), 4% sodium bicarbonate (2×25 mL), water (25 mL), and brine (25 mL). The combined organic layers were concentrated under reduced pressure and the residue was purified via column chromatography on silica gel (80 g, eluting with 0-10% CMA/chloroform), concentrated under reduced pressure, and recrystallized from diethyl ether to afford 0.45 g of ethyl 1-isobutyl-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-ylcarbamate as white crystals, mp 120-121° C.

Workup

  1. temperaturemaintained at ambient temperature for 16 hours
  2. washwashed sequentially with water (25 mL), 4% sodium bicarbonate (2×25 mL), water (25 mL), and brine (25 mL)
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. customthe residue was purified via column chromatography on silica gel (80 g, eluting with 0-10% CMA/chloroform)
  5. concentrationconcentrated under reduced pressure
  6. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-1624216fb85644ff9d7ba53032f4ffca
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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