3,4-Difluorobenzoyl chloride → HCID 57717557, compound

HRID 1984459Notes

Reaction equation

HRID 1984459 reaction equation
[NH2:1][C:2]([CH3:22])([CH3:21])[CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[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:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[F:33])[C:27](Cl)=[O:28]>>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][CH3:20])[C:4]([CH2:3][C:2]([NH:1][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:32]([F:33])=[C:24]([F:23])[CH:25]=3)([CH3:21])[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 27245193,4-Difluorobenzoyl chlorideHCID 57717565HCID 57717565, compound

Product 1

HCID 57717557HCID 57717557, compoundYield 79.1%

Procedure

Using the method of Example 601, 1-(2-amino-2-methylpropyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (prepared as described in Example 64, 770 mg, 2.59 mmol) was reacted with 3,4-difluorobenzoyl chloride (1.14 g, 6.48 mmol). The crude product was purified as described in Example 601 to provide 896 mg of N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]-3,4-difluorobenzamide as a white solid, mp 165-166° C. MS (APCI) m/z 438 (M+H)+; Anal. Calcd for C24H25F2N5O: C, 65.89; H, 5.76; N, 16.01. Found: C, 65.84; H, 5.58; N, 15.92.

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-be746a80ddf84f648f19c86b7b4faa38
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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