2-Aminophenylboronic acid hydrochloride → HCID 11965290, compound

HRID 1360591Notes

Reaction equation

HRID 1360591 reaction equation
Br[C:2]1[C:3]([C:17]#[N:18])=[N:4][N:5]([CH2:13][CH2:14][O:15][CH3:16])[C:6]=1[CH2:7][C:8]([C:11]#[N:12])([CH3:10])[CH3:9].Cl.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O>>[NH2:18][C:17]1[C:3]2=[N:4][N:5]([CH2:13][CH2:14][O:15][CH3:16])[C:6]([CH2:7][C:8]([CH3:10])([CH3:9])[C:11]#[N:12])=[C:2]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=1

Participants

3

Reactant 2

HCID 164270902-Aminophenylboronic acid hydrochlorideHCID 66958354HCID 66958354, compound

Product 1

HCID 11965290HCID 11965290, compoundYield 41.8%

Procedure

A modification of the method described in Part B of Example 1283 was used to couple 4-bromo-5-(2-cyano-2-methylpropyl)-1-(2-methoxyethyl)-1H-pyrazole-3-carbonitrile (1.56 g, 5.00 mmol) with 2-aminophenylboronic acid hydrochloride (1.73 g, 10.0 mmol). The reaction was completed in one hour. The coupling product was purified by IFC (silica cartridge, eluting with 50% to 90% ethyl acetate in hexane). The reaction with hydrogen chloride was heated at reflux for two hours and allowed to cool to room temperature overnight. 3-[4-Amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-2,2-dimethylpropanenitrile (676 mg) was obtained as white crystals, mp 206-208° C.

Workup

  1. customThe coupling product was purified by IFC (silica cartridge, eluting with 50% to 90% ethyl acetate in hexane)
  2. customThe reaction with hydrogen chloride
  3. temperaturewas heated
  4. temperatureat reflux for two hours

Sources & evidence

ORD record
ord-642ef19437de4c3fbd376f76c976d0f0
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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