Acetyl chloride → HCID 11842651, compound

HRID 2283929Notes

Reaction equation

HRID 2283929 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.[C:27](Cl)(=[O:29])[CH3:28]>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:27](=[O:29])[CH3:28])[CH:23]([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 669586022-Methyl-1-(2-methylpropyl)-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 11842651HCID 11842651, compoundYield 56%

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. Acetyl chloride (0.255 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 0-20% CMA/chloroform), concentrated under reduced pressure, and recrystallized from diethyl ether to yield 0.49 g of N-(1-isobutyl-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-yl)acetamide as white crystals, mp 130-131° 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 0-20% CMA/chloroform)
  5. concentrationconcentrated under reduced pressure
  6. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-9c8bf05595334c7cbdc18a16ee96b3b5
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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