Potassium Carbonate → HCID 86628442, compound

HRID 2426374Notes

Reaction equation

HRID 2426374 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][NH:21][O: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.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][NH:21][O: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]([C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 86628443HCID 86628443, compound

Product 1

HCID 86628442HCID 86628442, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A stream of nitrogen was bubbled through a stirring suspension of 1-{4-amino-7-bromo-2-[(methoxyamino)methyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}-2-methylpropan-2-ol (0.590 g, 1.49 mmol),3-pyridineboronic acid (0.220 g, 1.79 mmol), and potassium carbonate (0.681 g, 4.93 mmol) in ethylene glycol dimethyl ether (10 mL) and water (5 mL) in a pressure vessel for 5 minutes. Dichlorobis(triphenylphosphine)palladium(III) (0.031 g, 0.045 mmol) was added and nitrogen was bubbled through for an additional 5 minutes. The pressure vessel was capped and placed in a 110° C. oil bath for 10 minutes. The resulting solution was cooled to ambient temperature and concentrated. The residue was purified by column chromatography using a HORIZON HPFC system (silica cartridge, eluting with 5-25% 1M ammonia/methanol in dichloromethane). The resulting yellow solid was crystallized from acetonitrile and isolated by filtration to yield 167 mg of 1-{4-amino-2-[(methoxyamino)methyl]-7-(pyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}-2-methylpropan-2-ol as a light yellow solid, mp 195-197° C.

Workup

  1. customnitrogen was bubbled through for an additional 5 minutes
  2. customThe pressure vessel was capped
  3. customplaced in a 110° C.
  4. customfor 10 minutes
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 5-25% 1M ammonia/methanol in dichloromethane)
  8. customThe resulting yellow solid was crystallized from acetonitrile
  9. customisolated by filtration

Sources & evidence

ORD record
ord-9c87319fd7404ecd8414f90394082605
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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