1,2-Dimethoxyethane → HCID 58970689, compound

HRID 598022Notes

Reaction equation

HRID 598022 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[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.[NH2:25][C:26]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+].COCCOC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:18])([CH3:19])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:32]3[CH:33]=[C:28]([CH:29]=[CH:30][CH:31]=3)[C:26]([NH2:25])=[O:27])=[CH:5][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 589706811-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol

Product 1

HCID 58970689HCID 58970689, compoundYield 14.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol (1.2 g, 3.0 mmol), (3-aminocarbonylphenyl)boronic acid (0.603 g, 3.65 mmol), potassium carbonate (1.4 g, 10.0 mmol), dichlorobis(triphenylphosphine)palladium(II)(0.021 g, 0.030 mmol), DME (13 mL), and water (7 mL) was stirred under a nitrogen atmosphere in a pressure vessel. The vessel was then sealed and heated at 110° C. for 64 hours and allowed to cool to room temperature. A precipitate formed and was isolated by filtration, washed with water and DME, and recrystallized from methanol (100 mL/900 mg). The crystals were isolated by filtration, washed with methanol, and dried in a vacuum oven at 65° C. to provide 191 mg of 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-7-yl]benzamide as an off-white solid, mp >250° C.

Workup

  1. customThe vessel was then sealed
  2. temperatureto cool to room temperature
  3. customA precipitate formed
  4. customwas isolated by filtration
  5. washwashed with water and DME
  6. customrecrystallized from methanol (100 mL/900 mg)
  7. customThe crystals were isolated by filtration
  8. washwashed with methanol
  9. customdried in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-4b315f756d0f4d00b5785dfe4acaae31
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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