3-Pyridinecarbonyl chloride, hydrochloride (1:1) → HCID 57717623, compound

HRID 1984458Notes

Reaction equation

HRID 1984458 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]([CH3:33])([CH3:32])[CH2:13][C:14]1[N:15]([CH2:28][CH2:29][O:30][CH3:31])[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(OCC)(=O)C>[NH2:27][C:18]1[C:17]2=[N:16][N:15]([CH2:28][CH2:29][O:30][CH3:31])[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)([CH3:33])[CH3:32])=[C:26]2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 57717558HCID 57717558, compound

Product 1

HCID 57717623HCID 57717623, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Using the method of Example 68, nicotinoyl chloride hydrochloride (668 mg, 4.75 mmol) was reacted with 1-(2-amino-2-methylpropyl)-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (470 mg, 1.5 mmol, prepared as described in Example 590). The crude product was purified by IFC (silica gel eluting with a gradient of 10 to 40% CMA in chloroform) to provide a pale yellow resin. The resin was refluxed with 35% ethyl acetate in hexanes (50 mL) and ethyl acetate (75 mL) and cooled to ambient temperature with stirring. The resulting solid was isolated by filtration, rinsed with 35% ethyl acetate in hexanes, and dried to provide 278 mg of N-{2-[4-amino-2-(methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}nicotinamide as a light beige solid, mp 212-214° C. MS (APCI) m/z 419 (M+H)+; Anal. Calcd for C23H26N6O2: C, 66.01; H, 6.26; N, 20.08. Found: C, 65.74; H, 6.50; N, 20.09.

Workup

  1. customThe crude product was purified by IFC (silica gel eluting with a gradient of 10 to 40% CMA in chloroform)
  2. customto provide a pale yellow resin
  3. customThe resulting solid was isolated by filtration
  4. washrinsed with 35% ethyl acetate in hexanes
  5. customdried

Sources & evidence

ORD record
ord-6239082dd207434daae82ee2efc424dc
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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