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Water → HCID 58970690, compound

HRID 598044
Notes
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Reaction equation

HRID 598044 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[OH:29][CH2:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=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]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])([CH3:18])[CH3:17])[C:10]=2[C:9]2[N:8]=[CH:7][C:6]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:30][OH:29])[CH:36]=3)=[CH:5][C:4]=2[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 58970687HCID 58970687, compound

Product 1

HCID 58970690HCID 58970690, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 11776
Triphenylphosphine
Catalyst
HCID 167845palladium(II) acetateCatalyst
HCID 10311-PropanolSolvent

Procedure

The method described in Example 152 was used to treat N-{2-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}methanesulfonamide (1.2 g, 2.55 mmol) and 3-(hydroxymethyl)benzeneboronic acid (0.58 g, 3.8 mmol) in 1-propanol (15 mL) with triphenylphosphine (20.0 mg, 0.0760 mmol), aqueous sodium carbonate (3.82 mL of 2 M), water (3 mL), and palladium (II) acetate (5.7 mg, 0.025 mmol) with the following modifications. The reaction mixture was heated at reflux overnight. The crude product was purified by automated flash chromatography (FLASH 40+M cartridge, eluting with 0% to 35% CMA in chloroform) followed by recrystallization from acetonitrile to provide 0.98 g of N-(2-{4-amino-2-(ethoxymethyl)-7-[3-(hydroxymethyl)phenyl]-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl}-1,1-dimethylethyl)methanesulfonamide as a white solid, mp 173-174° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customThe crude product was purified by automated flash chromatography (FLASH 40+M cartridge, eluting with 0% to 35% CMA in chloroform)
  4. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-816252369d1748a4867ff9475b561a58
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes