Water → 1-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

HRID 598030

Reaction equation

HRID 598030 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25](B(O)O)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:25]3[CH:24]=[N:23][C:32]4[C:27]([CH:26]=3)=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:5][C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 589706911-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

Product 1

HCID 589707151-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-olYield 52.1%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

The method described in Example 152 was used to treat 1-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol (1.0 g, 2.7 mmol) and 3-quinolineboronic acid (0.52 g, 3.0 mmol) in 1-propanol (10 mL) with triphenylphosphine (21.6 mg, 0.0820 mmol), aqueous sodium carbonate (4.1 mL of 2 M), water (2 mL), and palladium (II) acetate (6.2 mg, 0.027 mmol) with the following modifications. The reaction mixture was heated at reflux for four hours. The crude product was purified by recrystallization from ethyl acetate to provide 0.58 g of 1-[4-amino-2-ethyl-7-(quinolin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as beige needles, mp >270° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for four hours
  3. customThe crude product was purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-02c4350769a44979b83638dbe14990fa
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Linked notes

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