4-Fluorobenzoyl chloride → HCID 57717513, compound

HRID 1360540Notes

Reaction equation

HRID 1360540 reaction equation
[NH2:1][C:2]([CH3:23])([CH3:22])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][O:20][CH3:21])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][O:20][CH3:21])[C:4]([CH2:3][C:2]([NH:1][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][C:25]([F:24])=[CH:26][CH:27]=3)([CH3:23])[CH3:22])=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 57717558HCID 57717558, compound

Product 1

HCID 57717513HCID 57717513, compoundYield 79.1%

Procedure

Using the general method of Example 599, 1-(2-amino-2-methylpropyl)-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (500 mg, 1.60 mmol, prepared as described in Example 590) was reacted with 4-fluorobenzoyl chloride (634 mg, 4.00 mmol). The crude product was purified by IFC (silica gel eluting with a gradient of 5 to 20% CMA in chloroform) followed by recrystallization from ethyl acetate/hexanes to provide 551 mg of N-{2-[4-amino-2-(methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}-4-fluorobenzamide as a white solid, mp 187-189° C. MS (ESI) m/z 436 (M+H)+; Anal. Calcd for C24H26FN5O2: C, 66.19; H, 6.02; N, 16.08. Found: C, 65.92; H, 5.93; N, 15.87.

Workup

  1. customThe crude product was purified by IFC (silica gel eluting with a gradient of 5 to 20% CMA in chloroform)
  2. customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6fb61ff05c794b8e8d6bb31c01e5e0c1
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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